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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
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)
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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 (CC BY 3.0).

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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.

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