Next Article in Journal
Linalool Exhibits Cytotoxic Effects by Activating Antitumor Immunity
Next Article in Special Issue
FACE Analysis as a Fast and Reliable Methodology to Monitor the Sulfation and Total Amount of Chondroitin Sulfate in Biological Samples of Clinical Importance
Previous Article in Journal
Synthesis and Antiproliferative Effects of Amino-Modified Perillyl Alcohol Derivatives
Previous Article in Special Issue
Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(5), 6683-6693; https://doi.org/10.3390/molecules19056683

Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
*
Author to whom correspondence should be addressed.
Received: 31 March 2014 / Revised: 9 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
Full-Text   |   PDF [279 KB, uploaded 18 June 2014]   |  

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. View Full-Text
Keywords: 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Jiang, R.; Zong, G.; Liang, X.; Jin, S.; Zhang, J.; Wang, D. Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides. Molecules 2014, 19, 6683-6693.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top