Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy
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- Doris Stafford
- 6 years ago
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1 Supporting Information: Dostie, Prévost and Guindon S-1 Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy Starr Dostie,, Michel Prévost *,, Philippe Mochirian, Kashif Tanveer, Nicholas Andrella, Ariana Rostami, Guillaume Tambutet,, and Yvan Guindon *,,, Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM), Montréal, Québec, H2W 1R7, Canada Department of Chemistry, Université de Montréal, Montréal, Québec, H3C 3J7, Canada Department of Chemistry, McGill University, Montréal, Québec, H3A 2K6, Canada Part I Computational Data Part II. 1 H and 13 C NMR Spectra Table of Contents for Part II: 1 H and 13 C NMR Spectra Product 8 ( 1 H and 13 C spectra)... 15, 16 Product 10 ( 1 H and 13 C spectra)... 17, 18 Product 9a&9b ( 1 H and 13 C spectra)... 19, 20 Product 11a&11b ( 1 H and 13 C spectra)... 21, 22 Product S1 ( 1 H and 13 C spectra)... 23, 24 Product S2 ( 1 H and 13 C spectra)... 25, 26 Product S3 ( 1 H and 13 C spectra)... 27, 28 Product 12 ( 1 H and 13 C spectra)... 29, 30 Product S4 ( 1 H and 13 C spectra)... 31, 32 Product S5 ( 1 H and 13 C spectra)... 33, 34 Product 14 ( 1 H and 13 C spectra)... 35, 36 Product 13a ( 1 H and 13 C spectra)... 37, 38 Product 13b ( 1 H and 13 C spectra)... 39, 40 Product 15a ( 1 H and 13 C spectra)... 41, 42 Product 15b ( 1 H and 13 C spectra)... 43, 44 Product 16 ( 1 H and 13 C spectra)... 45, 46 Product 17 ( 1 H and 13 C spectra)... 47, 48 Product 18 ( 1 H and 13 C spectra)... 49, 50 Product 19 ( 1 H and 13 C spectra)... 51, 52 Product 20 ( 1 H and 13 C spectra)... 53, 54 Product 21 ( 1 H and 13 C spectra)... 55, 56 Product 22 ( 1 H and 13 C spectra).57, 58, 59 Product 23 ( 1 H and 13 C spectra)... 60, 61 Product 24 ( 1 H and 13 C spectra)... 62, 63 Product 25 ( 1 H and 13 C spectra)... 64, 65 Product 26 ( 1 H and 13 C spectra)... 66, 67 Product 27 ( 1 H and 13 C spectra)... 68, 69 Product 28 ( 1 H spectrum) Product S6 ( 1 H and 13 C spectra)... 71, 72 Product 29 ( 1 H and 13 C spectra) , 74 Product S7 ( 1 H spectrum)... 75, 76 Product S8 ( 1 H and 13 C spectra) , 78 Product 30 ( 1 H and 13 C spectra) , 80 Product 31 ( 1 H and 13 C spectra) , 82
2 Supporting Information: Dostie, Prévost and Guindon S-2 Product S9 ( 1 H and 13 C spectra) , 84 Product S10 ( 1 H and 13 C spectra) , 86 Product 32 ( 1 H and 13 C spectra) , 88 Product 33 ( 1 H and 13 C spectra) , 90 Product S11 ( 1 H and 13 C spectra) , 92 Product S12 ( 1 H and 13 C spectra) , 94 Product 34 ( 1 H and 13 C spectra) , 96 Product 35 ( 1 H and 13 C spectra) , 98 Product S13 ( 1 H spectrum) Product S14 ( 1 H and 13 C spectra) , 101 Product S15 ( 1 H and 13 C spectra) , 103 Product S16 ( 1 H and 13 C spectra) , 105 Product S17 ( 1 H and 13 C spectra) , 107 Product 36 ( 1 H and 13 C spectra) , 109 Product 37 ( 1 H and 13 C spectra) , 111 Product 38 ( 1 H and 13 C spectra) , 113 Product 39 ( 1 H and 13 C spectra) , 115 Product 40 ( 1 H and 13 C spectra) , 117 Product 41 ( 1 H and 13 C spectra) 118, 119, 120 Product S18 ( 1 H and 13 C spectra) , 122 Product S19 ( 1 H and 13 C spectra) , 124 Product 42 ( 1 H and 13 C spectra) , 126 Product 43 ( 1 H and 13 C spectra) , 128 Product 44 ( 1 H and 13 C spectra) , 130 Product S20 ( 1 H and 13 C spectra) , 132 Product 45 ( 1 H and 13 C spectra) , 134 Product 46 ( 1 H and 13 C spectra) , 136 Product 47 ( 1 H and 13 C spectra) , 138 Product S21 ( 1 H and 13 C spectra) , 140 Product S22 ( 1 H and 13 C spectra) , 142 Product 48 ( 1 H and 13 C spectra) , 144 Product 49 ( 1 H and 13 C spectra) , 146 Product S23 ( 1 H and 13 C spectra) , 148 Product S24 ( 1 H and 13 C spectra) , 150 Product 50 ( 1 H and 13 C spectra) , 152 Product 51 ( 1 H and 13 C spectra) , 154 Product S25 ( 1 H and 13 C spectra) , 156 Product S26 ( 1 H and 13 C spectra) , 158 Product 52 ( 1 H and 13 C spectra) , 160 Product S27 ( 1 H and 13 C spectra) , 162 Product S28 ( 1 H and 13 C spectra) , 164 Product 53 ( 1 H and 13 C spectra) , 166 Product S29 ( 1 H and 13 C spectra) , 168 Product 54 ( 1 H and 13 C spectra) , 170 Product 55 ( 1 H and 13 C spectra) , 172 Product S30 ( 1 H and 13 C spectra) , 174 Product 56 ( 1 H and 13 C spectra) , 176 Part III. Stereochemical Proofs Part IV. X-ray for References
3 Supporting Information: Dostie, Prévost and Guindon S-3 Part I: Computational Data DFT Method and Details QM calculations were performed in Gaussian The geometry and transition state optimizations (Berny algorithm) were achieved with tight SCF convergence, an ultrafine integral grid and a fine CPHF grid (keywords: Int(Grid=Ultrafine) CPHF(Grid=Fine)). All the possible conformations of the C1-C2 bond and the isopropyl side chain where considered and optimized for the formation of the major and minor diastereoisomers. The energies presented in the paper and the supporting information are from fully optimized structures at the M062X 2,3 level of theory using the G** basis set with the LANL2DZpd 4,5 effective core potential. Calculation in solvents (THF) were performed with transition state or geometry using the polarizable continuum model (PCM). 6 Pseudopotential for Iodine 4,5 : **** I 0 LANL2DZ P E D **** Frequency calculations were performed at K (1 atm) on every optimized structure to determine their nature, transition states or intermediates, and to determine free energy values (1 Hartree = kcal mol 1 ). As mentioned in the manuscript, free energy corrections were applied using Truhlar s quasiharmonic approximation. 7,8,9 Intrinsic reaction coordinate calculations using the local quadratic approximation (LQA) ensured that the TS led either to reported product (or product complex) and reactant (or reactant complex) without encountering any energy barriers. The wave function stability was confirmed for all stationary structures. Orbital stabilization energies and Wiberg bond orders 10 were obtained from the NBO theory (version 3.1) implemented in Gaussian 09. Gibbs free energies of activation ( G ) correspond to the energy difference between the lowest energy anti- and syn-predictive TS. The ratio of products was calculated from equation 1 (R= kcal mol -1 K -1, T=273.15). [2,3-anti] G = RT*ln (eq 1) [2,3-syn]
4 Supporting Information: Dostie, Prévost and Guindon S-4 Gibbs Free Energy Profile for the Addition of Silylated Nucleobase (Uracil(TMS) 2 ) (M062X-6-311*G++-Lanl2dzpd) to Iodothioethers 6ab in THF:
5 Supporting Information: Dostie, Prévost and Guindon S-5 Free Gibbs Energies (Ha) Profile: Species (Gibbs Free Energies Relative to 6a) Gibbs Free Energies (Ha) (kcal/mol) TSepi TS-epi ( ) [6a ( ) + I ( )] a I 6a I ( ) [6a ( ) + I ( )] a TS D PC-1,2- anti 6a ( ) and I ( ) (energies are represented relative to this energy point) TS D ( ) [6a ( ) + Uracil(TMS) 2 ( )] PC-1,2-anti ( ) [6a ( ) + Uracil(TMS) 2 ( )] b I 6b I ( ) [6a ( ) + I ( )] b 6b ( ) [6a ( ) + I ( )] TS A PC-1,2- syn TS A ( ) [6a ( ) + Uracil(TMS) 2 ( )] PC-1,2-syn ( ) [6a ( ) + Uracil(TMS) 2 ( )] Energies (M06-2X/6-311+G**/lanl2dzpd/PCM=THF) and Cartesian Coordinates TSepi SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: 38.8i cm 1 C C H C H S C H H H H I C H H H C H H H I F
6 Supporting Information: Dostie, Prévost and Guindon S-6 6a I SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none C C H C H S C H H H H I C H H H C H H H I F a SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none C C H C H S C H H H H C
7 Supporting Information: Dostie, Prévost and Guindon S-7 H H H C H H H I F TS D Optimized at M06-2X/6-311+G**/lanl2dzpd/Gas phase (solvation calculation PCM=THF performed on the final geometry) SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree solvation energy: hartree quasiharmonic free energy correction: hartree imaginary frequency: 230.3i cm 1 O C H C H C H S C H H H C N Si I C H C H N C O Si C H H H C H
8 Supporting Information: Dostie, Prévost and Guindon S-8 H H C H H H C H H H C H H H C H H H C H H H C H H H F PC-1,2-anti SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none O C H C S C H H H C N Si I C H C H
9 Supporting Information: Dostie, Prévost and Guindon S-9 N C O Si H C H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H F b I SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none C C H
10 Supporting Information: Dostie, Prévost and Guindon S-10 C H S C H H H H I C H H H C H H H I F b SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none C C H C H S C H H H H I C H H H C H H H F TS A Optimized at M06-2X/6-311+G**/lanl2dzpd/Gas phase
11 Supporting Information: Dostie, Prévost and Guindon S-11 (solvation calculation PCM=THF performed on the final geometry) SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree solvation energy: hartree quasiharmonic free energy correction: hartree imaginary frequency: 82.2i cm 1 O C H C H C H S C H H H C N Si I C H C H N C O Si C H H H C H H H C H H H C H H H C H
12 Supporting Information: Dostie, Prévost and Guindon S-12 H H C H H H C H H H C H H H F PC-1,2-anti SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none O C H C H C H S C H H H C N Si I C H C H N C O Si C H H H C
13 Supporting Information: Dostie, Prévost and Guindon S-13 H H H C H H H C H H H C H H H C H H H C H H H C H H H F Uracil(TMS) 2 (low energy conformation, see reference Guindon et al. JOC 2014) 11 SCF energy: hartree zero-point correction: hartree enthalpy correction: hartree free energy correction: hartree quasiharmonic free energy correction: hartree imaginary frequency: none O C N Si C H C H N C O Si C H H H
14 Supporting Information: Dostie, Prévost and Guindon S-14 C H H H C H H H C H H H C H H H C H H H
15 Supporting Information: Dostie, Prévost and Guindon S-15 1 H-NMR (500 MHz, CDCl 3 ) CDCl f1 (ppm)
16 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
17 6.64 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl3 ) SEt F 10 SEt
18 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) SEt F 10 SEt CDCl 3
19 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3) CDCl3
20 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl3 ) CDCl3
21 4.97 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
22 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl3 ) CDCl3
23 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
24 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
25 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
26 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
27 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
28 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
29 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
30 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) C-NMR (125 MHz, CDCl 3) CDCl3
31 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
32 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
33 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3) OBn OBn TBSO S5 F
34 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) OBn TBSO S5 OBn F CDCl3
35 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3) CDCl3
36 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
37 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
38 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
39 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
40 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
41 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) H-NMR (500 MHz, CDCl 3)
42 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
43 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) H-NMR (500 MHz, CDCl 3)
44 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
45 Supporting Information: Dostie, Prévost and Guindon S-45 1 H-NMR (500 MHz, CDCl 3 )
46 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
47 Supporting Information: Dostie, Prévost and Guindon S-47 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
48 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
49 Supporting Information: Dostie, Prévost and Guindon S-49 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
50 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
51 Supporting Information: Dostie, Prévost and Guindon S-51 1 H-NMR (500 MHz, D 2 O) D 2O
52 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
53 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3) CDCl3
54 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
55 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3)
56 12.09 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3) CDCl3
57 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) H-NMR (500 MHz, CD 3OD) CD3OD
58 2.94 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, (CD 3)2SO) (CD3)2SO
59 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
60 Supporting Information: Dostie, Prévost and Guindon S-60 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
61 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
62 Supporting Information: Dostie, Prévost and Guindon S-62 1 H-NMR (500 MHz, CDCl 3 )
63 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
64 Supporting Information: Dostie, Prévost and Guindon S-64 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
65 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
66 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) H-NMR (500 MHz, CDCl 3)
67 12.69 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) C-NMR (125 MHz, CDCl 3) CDCl3
68 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) H-NMR (500 MHz, CDCl 3)
69 12.62 Supporting Information: Dostie, Prévost and Guindon S f1 (ppm) C-NMR (125 MHz, CDCl 3) CDCl3
70 Supporting Information: Dostie, Prévost and Guindon S-70 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
71 Supporting Information: Dostie, Prévost and Guindon S-71 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
72 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
73 3.14 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3) CDCl3
74 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
75 Supporting Information: Dostie, Prévost and Guindon S-75 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
76 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
77 Supporting Information: Dostie, Prévost and Guindon S-77 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
78 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
79 Supporting Information: Dostie, Prévost and Guindon S-79 1 H-NMR (500 MHz, CDCl 3 ) OBz OBz Me OTES 30 CDCl 3
80 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) OBz OBz Me OTES 30 CDCl 3
81 Supporting Information: Dostie, Prévost and Guindon S-81 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
82 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
83 Supporting Information: Dostie, Prévost and Guindon S-83 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
84 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
85 Supporting Information: Dostie, Prévost and Guindon S-85 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
86 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
87 Supporting Information: Dostie, Prévost and Guindon S-87 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
88 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
89 Supporting Information: Dostie, Prévost and Guindon S-89 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
90 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
91 Supporting Information: Dostie, Prévost and Guindon S-91 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
92 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
93 Supporting Information: Dostie, Prévost and Guindon S-93 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
94 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
95 Supporting Information: Dostie, Prévost and Guindon S-95 1 H-NMR (500 MHz, CDCl 3 ) CDCl 3
96 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
97 Supporting Information: Dostie, Prévost and Guindon S-97 1 H-NMR (500 MHz, CD 3 OD) CD 3OD
98 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, Acetone-d 6 ) Acetone-d 6 Acetone-d 6
99 Supporting Information: Dostie, Prévost and Guindon S-99 1 H-NMR (500 MHz, CDCl 3 ) O O HO Me S13 CDCl 3
100 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
101 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
102 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
103 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
104 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
105 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
106 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
107 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
108 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
109 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
110 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
111 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
112 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
113 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
114 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
115 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
116 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
117 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
118 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CD 3 OD) CD 3OD
119 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, (CD 3 ) 2 SO) (CD 3) 2SO
120 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
121 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
122 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
123 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
124 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
125 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CD 3 OD) CD 3OD
126 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
127 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
128 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
129 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
130 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
131 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
132 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
133 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
134 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
135 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CD 3 OD) CD 3OD
136 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
137 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
138 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
139 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
140 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
141 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
142 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
143 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
144 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
145 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
146 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
147 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
148 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
149 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
150 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
151 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CD 3 OD) CD 3OD
152 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 CN) CD 3CN CD 3CN
153 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
154 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
155 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
156 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
157 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
158 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
159 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CD 3 OD) CD 3OD
160 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
161 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
162 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
163 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
164 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
165 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, (CD 3 ) 2 CO) (CD 3 ) 2 CO
166 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CD 3 OD) CD 3OD
167 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
168 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
169 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
170 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
171 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
172 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
173 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
174 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
175 Supporting Information: Dostie, Prévost and Guindon S H-NMR (500 MHz, CDCl 3 ) CDCl 3
176 Supporting Information: Dostie, Prévost and Guindon S C-NMR (125 MHz, CDCl 3 ) CDCl 3
177 Supporting Information: Dostie, Prévost and Guindon S-177 Part III : Stereochemical Proofs In all cases, the selectivities were determined by 1 H NMR spectroscopic analysis of the unpurified reaction mixtures. The C1 C2 relative configurations of the synthesized nucleoside analogues were determined by relevant nuclear Overhauser effect (NOE) enhancements (2D NOESY), 1 H NMR coupling constant data and correlations of chemical shifts. The peaks in the 1 H NMR spectra were assigned using 1 H/ 1 H COSY experiments, chemical shifts, and coupling constants. Proof of structure for the C1'-C2' relative stereochemistry were provided by NOESY experiments. Nucleoside analogues and are known compounds. Relevant NOESY data for nucleoside analogues 19, 22, 25, 27. Relevant NOESY data for nucleoside analogue 35 including its X-ray.
178 Supporting Information: Dostie, Prévost and Guindon S-178 Relevant NOESY data for nucleoside analogues 41, 42, and 46. Proof of N9 regiochemistry of the 6-Cl-purine ring was determined from HSQC and HMBC experiments. Relevant HSQC, HMBC and NOESY data for nucleoside analogues 48. Relevant NOESY data for nucleoside analogues 50 and 52.
179 Supporting Information: Dostie, Prévost and Guindon S-179 Relevant NOESY data for nucleoside analogues 53, 54 and 56. A strong coupling between H3 and the C2-Me group was confirmed by NOESY for compound 29.
180 Supporting Information: Dostie, Prévost and Guindon S-180 Part IV. X-ray information for compound 35 Single crystals of C 48.5 H 70 F 4 N 8 O 16.5 S 4 were prepared from a mixture of ethyl acetate, methanol and hexanes. A suitable crystal was selected and mounted on a diffractometer. The crystal was kept at 100 K during data collection. Using Olex2, 14 the structure was solved with the XT 15 structure solution program using Direct Methods and refined with the XL 16 refinement package using Least Squares minimization. Crystal Data for C 48.5 H 70 F 4 N 8 O 16.5 S 4 (M = g/mol): monoclinic, space group P21 (no. 4), a = (3) Å, b = (4) Å, c = (4) Å, β = (10), V = (13) Å3, Z = 2, T = 100 K, µ(gakα) = mm-1, Dcalc = g/cm3, reflections measured ( Θ ), unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (all data). Four molecules and a half methanol were found by asymmetric unit. Empirical formula C 48.5 H 70 F 4 N 8 O 16.5 S 4 Formula weight Temperature/K 100 Crystal system monoclinic Space group P2 1 a/å (3) b/å (4) c/å (4) α/ 90 β/ (10) γ/ 90 Volume/Å (13) Z 2 ρ calc g/cm µ/mm F(000) Crystal size/mm Radiation GaKα (λ = ) 2Θ range for data collection/ to Index ranges -15 h 15, -17 k 18, -21 l 21 Reflections collected Independent reflections [R int = , R sigma = ]
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