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

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·H(2)O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-d-mannopyranosides directly in 80%~90% yields....

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Detalles Bibliográficos
Autores principales: Jiang, Rui, Zong, Guanghui, Liang, Xiaomei, Jin, Shuhui, Zhang, Jianjun, Wang, Daoquan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270901/
https://www.ncbi.nlm.nih.gov/pubmed/24858100
http://dx.doi.org/10.3390/molecules19056683
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author Jiang, Rui
Zong, Guanghui
Liang, Xiaomei
Jin, Shuhui
Zhang, Jianjun
Wang, Daoquan
author_facet Jiang, Rui
Zong, Guanghui
Liang, Xiaomei
Jin, Shuhui
Zhang, Jianjun
Wang, Daoquan
author_sort Jiang, Rui
collection PubMed
description 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·H(2)O 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.
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spelling pubmed-62709012018-12-21 Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides Jiang, Rui Zong, Guanghui Liang, Xiaomei Jin, Shuhui Zhang, Jianjun Wang, Daoquan Molecules Article 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·H(2)O 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. MDPI 2014-05-22 /pmc/articles/PMC6270901/ /pubmed/24858100 http://dx.doi.org/10.3390/molecules19056683 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Jiang, Rui
Zong, Guanghui
Liang, Xiaomei
Jin, Shuhui
Zhang, Jianjun
Wang, Daoquan
Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title_full Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title_fullStr Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title_full_unstemmed Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title_short Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
title_sort direct 2,3-o-isopropylidenation of α-d-mannopyranosides and the preparation of 3,6-branched mannose trisaccharides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270901/
https://www.ncbi.nlm.nih.gov/pubmed/24858100
http://dx.doi.org/10.3390/molecules19056683
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