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Direct 2,3-O-isopropylidenation of α-D-mannopyranosides and the preparation of 3,6-branched mannose trisaccharides.

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.

SUBMITTER: Jiang R 

PROVIDER: S-EPMC6270901 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Direct 2,3-O-isopropylidenation of α-D-mannopyranosides and the preparation of 3,6-branched mannose trisaccharides.

Jiang Rui R   Zong Guanghui G   Liang Xiaomei X   Jin Shuhui S   Zhang Jianjun J   Wang Daoquan D  

Molecules (Basel, Switzerland) 20140522 5

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. ...[more]