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

Synthesis of 3-O-Benzoyl-1 ,2-O-isopropylidene-a-D-allofuranose and Its Dimesylated Derivative
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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.
出处 《Transactions of Tianjin University》 EI CAS 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).
关键词 3-O-benzoyl-1. 2-O-isopropylidene-α-D-allofuranose OXIDATION reduction - selective hydrolysis dimesylation 3-O-苯甲酰-1,2-O-异亚丙基-α-D-同分异构呋喃糖 二甲磺酸盐衍生物 氧化反应 合成
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  • 1Urata,H. Yakugaku Zasshi . 1999

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