Thymine → HCID 11813811, compound

HRID 1720231Notes

Reaction equation

HRID 1720231 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].C[Si](C)(C)N[Si](C)(C)C.C(O[C@@H:23]1[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:55])[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:24]1[O:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)C>>[C:26]([O:25][C@@H:24]1[C@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:44]([CH2:46][O:47][C:48](=[O:55])[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[O:45][C@H:23]1[N:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 1135ThymineHCID 13838HexamethyldisilazaneHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 11813811HCID 11813811, compound

Procedure

The title compound was prepared by a 5-step sequence reaction. Thymine (12,6 g) was treated with hexamethyldisilazane and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (50 g) was added. The 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)thymine obtained was treated with sodium methoxide and gave 1-(β-D-ribofuranosyl)thymine (23 g). Then said substance was treated with tritylchloride and methylsulfonylchloride and 1-(2',3'-di-O-methylsulfonyl-5'-O-trityl-β-D-ribofuranosyl)thymine (39 g) was obtained. Said substance was treated with sodium hydroxide and gave the title compound 1-(2'-3'-anhydro-5'-O-trityl-β-D-lyxofuranosyl)thymine (VSB-020) 19.2 g. Yield 43%. 1H-NMR (DMSO-d6) δ: 1.66 (s, 3H, 5-CH3), 3.24-3.34 (m, 2H, 5'-H), 4.08 (s, 2H, 2'-H and 3'-H), 4.25 (t, 1H, 4'-H), 6.13 (s, 1H, 1'-H), 7.30-7.45 (m, 16H, trityl H and 6-H), 14.46 (s, 1H, N--H).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-90b5ef79de4f45e6a72bda10bcee4065
Source dataset
uspto-grants-1996_04
Patent number
US05506215

Reaction notes

Loading…