Synthesis of protected p-methoxyphenyl D-galactopyranosyl (α1 4)-(D-galactopyranosyl)-(β1 3)-2-deoxy-2-acetamido-D-glucopyranoside
10.16781/j.0258-879x.2016.02.0145
- Author:
Lei HUANG
1
Author Information
1. Department of Organic Chemistry, School of Pharmacy, Second Military Medical University
- Publication Type:Journal Article
- Keywords:
Bacillus anlhracis;
Chemosynlhesis;
Glycosylation;
Trisaccharides
- From:
Academic Journal of Second Military Medical University
2016;37(2):145-152
- CountryChina
- Language:Chinese
-
Abstract:
Objective To synthesize fully protected ρ methoxyphenyl D galactopyranosy (α1 4) (D galactopyranosyl) (β1 3)-2-deoxy 2 acctamido D glucopyranosidc. Methods With D galactose and D glucosamine hydrochloride used as the initial compounds, we stereoselectively and efficiently synthesized p-methoxyphenyl 2, 3,4, 6-tetra-O-acetyl-D-galactopyranosyl (α1 4) (2, 3, 4, 6 tetra Obenzyl D galactopyranosyl)-(β1 3) 6bcnzyl-2-deoxy-2-acetamido-β-D glucopyranosidc (1) by glucosinolates glycosylation and Schmidt glycosylation. Results Our method efficiently produced the target compound, and the structures of the main intermediates and target compound were confirmed by1HMNR,13CMNR and MS. Conclusion We have established a simple synthesis method with high universal property for target compound; additionally, the protective base is easily removable. Our method is applicable for the synthesis of various oligosaccharides.
