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
Molecules 2014, 19(5), 6683-6693; doi:10.3390/molecules19056683
Article

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

, , , , *  and
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)
View Full-Text   |   Download PDF [279 KB, uploaded 18 June 2014]   |   Browse Figures

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.
Keywords: 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide 2,3-O-isopropylidenation; α-D-mannosides; trisaccharide
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Supplement

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

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