| Synthesis of 3-O-Benzoyl-1 ,2-O-isopropylidene-a-D-allofuranose and Its Dimesylated Derivative |
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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，School of Chemical Engineering and Technology，Tianjin University，Tianjin 300072，China，School of Chemical Engineering and Technology，Tianjin University，Tianjin 300072，China，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 a-D-glucofuranose (1) was oxidated with CrO;-Pyridine complex. Oxidated product and its hydrate were separated and were reduced together to synthesize diisopro-pylidenated a-D-allofuranose (3 ). The yield of 3 increased by 8% than that with only oxidated prod-uct as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-l ,2-O-isopropylidene-a-D-allofuranose (5) and its dimesylated deriva-tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed by 'H-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, re-duction and other procedures were practical and had application potential.
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Synthesis of 3-O-Benzoyl-1 ,2-O-isopropylidene-a-D-allofuranose and Its Dimesylated Derivative |
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| ZHANG Weihong MENG Xiangqi FENG Yaqing,LIU Yunhua School of Chemical Engineering and Technology,Tianjin University,Tianjin ,China.Synthesis of 3-O-Benzoyl-1 ,2-O-isopropylidene-a-D-allofuranose and Its Dimesylated Derivative[J].Transactions of Tianjin University,2005(6). |
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| Authors: | ZHANG Weihong MENG Xiangqi FENG Yaqing LIU Yunhua School of Chemical Engineering and Technology Tianjin University Tianjin China |
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| Institution: | ZHANG Weihong MENG Xiangqi FENG Yaqing,LIU Yunhua School of Chemical Engineering and Technology,Tianjin University,Tianjin 300072,China |
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| Abstract: | Diisopropylidenated a-D-glucofuranose (1) was oxidated with CrO;-Pyridine complex. Oxidated product and its hydrate were separated and were reduced together to synthesize diisopro-pylidenated a-D-allofuranose (3 ). The yield of 3 increased by 8% than that with only oxidated prod-uct as reduction substrate. Benzoylated derivative of 3 was selectively hydrolyzed and dimesylated to synthesize 3-O-benzoyl-l ,2-O-isopropylidene-a-D-allofuranose (5) and its dimesylated deriva-tive respectively. The overall yield of 5 from 1 was 36%. Each step and final products were analyzed by 'H-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, re-duction and other procedures were practical and had application potential. |
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| Keywords: | 3-O-benzoyl-l 2-O-isopropylidene-(?)-D-allofuranose oxidation reduction selective hydrolysis: dimesylation |
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