Synthesis of D-Mannoheptol via the Oxidation of an Olefinated Sugar Using Phenyliodine(Ⅲ) Diacetate

doi:10.3724/SP.J.1095.2012.00253

Chinese Journal of Applied Chemistry

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Synthesis of D-Mannoheptol via the Oxidation of an Olefinated Sugar Using Phenyliodine(Ⅲ) Diacetate

CHENG Jie^*, ZHAI Hong, BAI Jun, LV Ling, SUN Bei

(Anhui Institute of Materia Medica,Hefei 230022,China)

Received:2011-06-14 Revised:2011-10-08 Published:2012-04-10 Online:2012-04-10

Abstract

Abstract: Firstly, 3,4,5,6,7-penta-O-benzyl-D-manno-hept-1-enitol was prepared from 2,3,4,5,6-penta-O-benzyl-D-mannose via Wittig reaction(yield 88%). The olefinated sugar was dihudroxylated to yield 3,4,5,6,7-penta-O-benzyl-D-mannoheptol(yield 65%) with the presence of phenyliodine(Ⅲ) diacetate(PIDA)/LiBr. Finally, D-mannoheptol was synthesized through debenzylation(yield 90%). The overall yield was about 51%. The method had the advantages of convenience and environmental friendly, which provided a new approach for the synthesis of such rare alditol.

Key words: D-mannoheptol, olefinated sugar, PIDA, dihydroxylated reaction

CLC Number:

O626.2

CHENG Jie*, ZHAI Hong, BAI Jun, LV Ling, SUN Bei. Synthesis of D-Mannoheptol via the Oxidation of an Olefinated Sugar Using Phenyliodine(Ⅲ) Diacetate[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2012.00253.

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Synthesis of D-Mannoheptol via the Oxidation of an Olefinated Sugar Using Phenyliodine(Ⅲ) Diacetate

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