Direct 2,3-O-isopropylidenation of α-D-mannopyranosides and the preparation of 3,6-branched mannose trisaccharides

Rui Jiang; Guanghui Zong; Xiaomei Liang; Shuhui Jin; Jianjun Zhang; Daoquan Wang

doi:10.3390/molecules19056683

Direct 2,3-O-isopropylidenation of α-D-mannopyranosides and the preparation of 3,6-branched mannose trisaccharides

Molecules. 2014 May 22;19(5):6683-93. doi: 10.3390/molecules19056683.

Authors

Rui Jiang¹, Guanghui Zong¹, Xiaomei Liang¹, Shuhui Jin¹, Jianjun Zhang², Daoquan Wang¹

Affiliations

¹ Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
² Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. zhangjianjun@cau.edu.cn.

Abstract

A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of α-D-mannopyranosides is reported. Treatment of various α-D-mannopyranosides with 0.12 equiv of the TsOH·H2O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-D-mannopyranosides directly in 80%~90% yields. Based on this method, a 3,6-branched α-D-mannosyl trisaccharide was prepared in 50.4% total yield using p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside as the starting material.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Sequence
Chemistry Techniques, Synthetic
Mannose / chemistry*
Methyl Ethers / chemistry
Molecular Structure
Trisaccharides / chemical synthesis*
Trisaccharides / chemistry
Vinyl Compounds / chemistry

Substances

Methyl Ethers
Trisaccharides
Vinyl Compounds
2-methoxypropene
Mannose