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Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position

✍ Scribed by Tsutomu Yokomatsu; Tomoyuki Sada; Takanori Shimizu; Shiroshi Shibuya

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
262 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

N-glycolylation of 3-(diethoxyphosphorothioyl)methyl-5-O-benzoyl-l-O-ethyl-2,3-dideoxyriboses 9b ~d 10b with silylated thymine in the presence of TiCI4 proceeded highly diastereoselectively (92% de) to give the corresponding ~nucleotide analogues in good yield. A remarkable neighboring group participation of the methytenephosphonothioate functionality was observed in the course of the lS-N-glycosylation.

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