二乙酰氧基亚碘酰苯氧化糖基烯合成D-甘露庚糖醇

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

以五苄基-D-甘露糖为原料,经Wittig反应制得D-甘露庚糖烯(产率88%),然后在二乙酰氧基亚碘酰苯/LiBr体系下催化氧化糖基烯制得五苄基-D-甘露庚糖醇(产率65%),最后脱苄基得到D-甘露庚糖醇(产率90%),总得率51%。方法简便、环保,可用于糖醇的合成。

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.