A Convenient Synthesis of S-Glycosyl Donors of D-Glucose and O-Glycosylations Involving the New Reagent

Kanoko TSUBOYAMA; Kazuyoshi TAKEDA; Katsumi TORII; Masako EBIHARA; Junko SHIMIZU; Ayumi SUZUKI; Noriko SATO; Kimio FURUHATA; Haruo OGURA

doi:10.1248/cpb.38.636

Kanoko TSUBOYAMA, Kazuyoshi TAKEDA, Katsumi TORII, Masako EBIHARA, Junko SHIMIZU, Ayumi SUZUKI, Noriko SATO, Kimio FURUHATA, Haruo OGURA

Author information

Keywords: S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate, O-glycosylation, S-glycosyl donor, 1-phenyltetrazol-5-thio moiety, silver triflate, glycosyl acceptor

JOURNAL FREE ACCESS

1990 Volume 38 Issue 3 Pages 636-638

DOI https://doi.org/10.1248/cpb.38.636

Details

Abstract

The synthesis of S-glycosyl donors from 2, 3, 4, 6-tetra-O-benzyl-α-glucopyranose (1) using S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (2) was carried out by a one-step reaction. One of the S-glycosyl donors, S-1-(1'-phenyl-1H-tetrazolyl)2, 3, 4, 6-tetra-O-benzyl-β-D-glucopyranose (3a), was utilized for glycosylation of glycosyl acceptors such as methanol or cholesterol using silver triflate as a promoter.

Corresponding author

Register with J-STAGE for free!