Preparation of unsaturated carbohydrates from methyl 4,6-O-benzylidene-3-chloro-3-deoxy- -D-allopyranoside, and their utility in the synthesis of sugars of biological importance |
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| Authors: | E H Williams W A Szarek J K Jones |
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| Affiliation: | 1. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China;2. Hubei Key Laboratory of Environmental and Health Effects of Persistent Toxic Substances, Institute of Environment and Health, Jianghan University, Wuhan 430056, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;4. Department of Ecology and Resources Engineering, He Tao College, Inner Mongolia 015000, China |
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| Abstract: | Methyl 4,6-O-benzylidene-β-d-erythro-hex-3-enopyranoside (2) is readily obtained from methyl 4,6-O-benzylidene-3-chloro-3-deoxy-β-d-allpyranoside (1). Treatment of compound 2 or its 2-O-acetyl derivative (3) with dilute hydrochloric acid in acetone affords the α,β-unsaturated ketone 4 in high yield. Examples of the synthetic utility of compound 4 are provided by its ready conversion into methyl 2,3,6-trideoxy-β-d-threo-hexopyranoside (methyl β-d-rhodinoside, 8) and the d-erythro isomer (methyl β-d-amicetoside, 13). |
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