Synthesis of 3-O-Benzoyl-1,2-O-isopropylidene-α-D-allofuranose and Its Dimesylated Derivative |
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引用本文: | 张卫红,孟祥启,冯亚青,刘云华.Synthesis of 3-O-Benzoyl-1,2-O-isopropylidene-α-D-allofuranose and Its Dimesylated Derivative[J].天津大学学报(英文版),2005,11(6):440-445. |
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作者姓名: | 张卫红 孟祥启 冯亚青 刘云华 |
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作者单位: | School of Chemical Engineering and Technology, Tianjin University Tianjin 300072, China |
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基金项目: | Supported by Tianjin Natural Science Foundation (No. 05YFJMJC09600). |
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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.
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关 键 词: | 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 |
收稿时间: | 2005-07-01 |
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