Synthesis of 3-O-Benzoyl-1 ,2-O-isopropylidene-a-D-allofuranose and Its Dimesylated Derivative  

作　　者：张卫红 孟祥启 冯亚青 刘云华 

机构地区：[1]School of Chemical Engineering and Technology,Tianjin University,Tianjin 300072,China

出　　处：《Transactions of Tianjin University》2005年第6期440-445,共6页天津大学学报（英文版）

基　　金：Supported by Tianjin Natural Science Foundation ( No. 05YFJMJC09600).

摘　　要：Diisopropylidenated α-D-glucofuranose （1） was oxidated with CrO3-pyridine complex. Oxidated product and its hydrate were separated and were reduced together to synthesize diisopropylidenated α-D-allofuranose （ 3）. The yield of 3 increased by 8% than that with only oxidated product as reduction substrate. Benzoylated derivative of 3 was selectively nydrolyzed and dimesylated to synthesize 3-O-benzoyl-1 .2- O- isopropylidene-α-D-allofuranose （ 5 ） and its dimesylated derivative respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed by ^1H-NMR spectra and other methods. The experiments showed that the influence of acetic acid concentration on selective hydrolysis was obvious. The hydrolysis yield was 81.8%. Oxidation. reduction and other procedures were practical and had application potential.Diisopropylidenated α-D-glucofuranose (1) was oxidated with CrO3-pyridine complex.Oxidated product and its hydrate were separated and were reduced together to synthesize diisopropylidenated α-D-allofuranose (3). The yield of 3 increased by 8% than that with only oxidated product as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-1,2- O- isopropylidene-α-D-allofuranose (5) and its dimesylated deriva tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were anal yzed by 1H-NMR spectra and other methods. The experiments showed that the influence of acetic acid concentration on selective hydrolysis was obvious. The hydrolysis yield was 81.8%. Oxidation, reduction and other procedures were practical and had application potential.

关 键 词：3-O-benzoyl-1. 2-O-isopropylidene-α-D-allofuranose OXIDATION reduction - selective hydrolysis dimesylation 

分 类 号：O625[理学—有机化学]