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....

Descripción completa

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
Descripción
Sumario: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.

Ejemplares similares