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

被引：7
|
作者：
Jiang, Rui [1 ]
Zong, Guanghui [1 ]
Liang, Xiaomei [1 ]
Jin, Shuhui [1 ]
Zhang, Jianjun [1 ]
Wang, Daoquan [1 ]
机构：
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
来源：
MOLECULES | 2014年 / 19卷 / 05期
关键词：
2,3-O-isopropylidenation; alpha-D-mannosides; trisaccharide; N-ACETYLGLUCOSAMINYLTRANSFERASE-I; CARBOHYDRATE-CHEMISTRY; LINKED GLYCANS; OLIGOSACCHARIDES; EFFICIENT; DEPROTECTION; PROTECTION; GLYCOSIDES; ACETALS; OCTYL;
D O I：
10.3390/molecules19056683
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of alpha-D-mannopyranosides is reported. Treatment of various a-D-mannopyranosides with 0.12 equiv of the TsOH:H2O and 2-methoxypropene at 70 degrees C gave 2,3-O-isopropylidenea- D-mannopyranosides directly in 80%similar to 90% yields. Based on this method, a 3,6-branched alpha-D-mannosyl trisaccharide was prepared in 50.4% total yield using p-nitrophenyl 2,3-Oisopropylidene- alpha-D-mannopyranoside as the starting material.
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页码：6683 / 6693
页数：11
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