Novel stereoselective entry to 2'-beta-carbon-substituted 2'-deoxy-4'-thionucleosides from 4-thiofuranoid glycals.
2'-Beta-methyl- and 2'-beta-hydroxymethyl-2'-deoxy-4'-thionucleosides have been synthesized through PhSeCl-mediated electrophilic glycosidation using 4-thiofuranoid glycals having carbon substituents at the C2-position as a glycosyl donor. Preparation of these glycals were carried out by means of the C2 lithiation of 1-chloro-4-thiofuranoid glycal with LTMP followed by the Birch reduction of the chlorine atom. [reaction: see text]
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. harakazu@pharm.showa-u.ac.jp
Shiina
Noriaki
N
Yoshimura
Yuichi
Y
Shimada
Hisashi
H
Hashimoto
Kyoko
K
Tanaka
Hiromichi
H
D015394:Molecular Structure; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism; D013872:Thionucleosides / Q000138:chemical synthesis*; D013876:Thiophenes / Q000737:chemistry*
C476353:4-thiofuranoid glycal; D012833:Siloxanes; D013872:Thionucleosides; D013876:Thiophenes