Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides

被引：20

作者：

Meng, Shuai ^{[1
]}

Zhong, Wenhe ^{[1
]}

Yao, Wang ^{[1
]}

Li, Zhongjun ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, Dept Chem Biol, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 08期

关键词：

ANOMERIC O-ALKYLATION; GALACTOSAMINE THIOGLYCOSIDE DONORS; INTRAMOLECULAR AGLYCON DELIVERY; AUREOLIC ACID ANTIBIOTICS; SOLID-PHASE SYNTHESIS; STEREOCONTROLLED SYNTHESIS; SELECTIVE GLYCOSYLATIONS; PROTECTED GLUCOSAMINE; ALPHA-GLYCOSIDE; REPEATING-UNIT;

D O I：

10.1021/acs.orglett.0c00732

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent beta-selectivity, resulting in 2-phenylseleno-2-deoxy-beta-galactosides and 2-phenylseleno-beta-mannosides which are good precursors of 2-deoxy-beta-galactosides and mannosides, respectively.

引用

页码：2981 / 2986

页数：6

共 123 条

[1] PREPARATION OF DISACCHARIDES HAVING A BETA-D-MANNOPYRANOSYL GROUP FROM N-PHTHALOYLLACTOSAMINE DERIVATIVES BY DOUBLE OR TRIPLE SN2 SUBSTITUTION [J].