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Communication | Special issue | Vol 52, No. 2, 2000, pp.515-518
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S56
Stereoselective C-Glycosylation of 2,3-Dideoxyribofuranosides Controlled by the Methylenephosphonothioate Functional Groups at the 3-Position

Tsutomu Yokomatsu, Tomoyuki Sada, Takanori Shimizu, and Shiroshi Shibuya*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

C-Glycosylation of 2,3-dideoxyribofuranoside (3) having a methylenephosphonothioate functional group at the 3-position with allylic carbonnucleophiles was examined in the presence of a variety of Lewis acids. Good β-selectivity with high chemical yield was observed upon using allyltrimethylsilane as a carbon nucleophile.