Stereoselective synthesis of 1'-C-carbon-subsituted 4'-thionucleosides from 4-thiofuranoid glycal.
PhSeCl or NIS-initiated glycosylation to 2-5, which were prepared through lithiation of 4-thiofuranoid glycal 1, proceeded stereoselectively to give the target 1'-C-carbon-substituted 4'-thiopyrimidine nucleosides. This synthetic method enabled us to synthesize 4'-thioanalogue 13 of nucleoside antibiotic angustmycin.
Haraguchi
K
K
School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142-8555, Japan.
Takahashi
H
H
Tanaka
H
H
D006031:Glycosylation; D012833:Siloxanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
C476353:4-thiofuranoid glycal; D012833:Siloxanes; D013876:Thiophenes