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Synthesis of a New Cerebroside Isolated from Typhonium giganteum Engl
作者姓名:陈雪松  吴毓林  陈迪华
作者单位:State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Acdemy of Sciences,Shanghai 20002,China Institute of Medicinal Plant Development,Chinese Academy of Medical Sciences & Peking Union Medical College,Beijing 100094,China,State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China,Institute of Medicinal Plant Development,Chinese Academy of Medical Sciences & Peking Union Medical College,Beijing 100094,China
基金项目:Project supported by the National Natural Science Foundation of China(No.29790126),Chinese Academy of Sciences(No.95-A1504-03)and the Ministry of Science and Technology of China(Nos.970211006-6,G2000077502).
摘    要:The stereoselecfive synthesis of typhoniside, a new cerebroside isolated from Typhonium giganteum Engl. was accomplished.Cerebrosides are a kind of glycolipids highly enriched on the surface of myelin-producing cells and are composed by C18-4,8-sphingadienine, a-hydroxy acid and a saccharide head. It was the first time that cerebrosides were isolated from this traditional Chinese medicine (TCM) by us. In this paper, C18-4,8-sphingadienine was synthesized from D-xylose via a SN2 type reaction, α-Hydroxy acid was prepared from (R)-4-hydroxyte-trahydrofuran-2-one, which in turn could be obtained from Lascorbic acid.

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Synthesis of a New Cerebroside Isolated from Typhonium giganteum Engl
CHEN,Xue-Song WU,Yu-Lin CHEN,Di-Hua State Key Laboratory of Bioorganic and Natural Products Chemistry.Synthesis of a New Cerebroside Isolated from Typhonium giganteum Engl[J].Chinese Journal of Chemistry,2003,21(7):937-943.
Authors:CHEN  Xue-Song WU  Yu-Lin CHEN  Di-Hua State Key Laboratory of Bioorganic and Natural Products Chemistry
Institution:CHEN,Xue-Song WU,Yu-Lin CHEN,Di-Hua State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China Institute of Medicinal Plant Development,Chinese Academy of Medical Sciences & Peking Union Medical College,Beijing 100094,China
Abstract:The stereoselective synthesis of typhoniside, a new cerebroside isolated from Typhonium giganteum Engl, was accomplished. Cerebrosides are a kind of glycolipids highly enriched on the surface of myelin‐producing cells and are composed by C18–4, 8‐sphingadienine, α‐hydroxy acid and a saccharide head. It was the first time that cerebrosides were isolated from this traditional Chinese medicine (TCM) by us. In this paper, C18–4, 8‐sphingadienine was synthesized from D‐xylose via a SN2 type reaction, α‐Hydroxy acid was prepared from (R)‐4‐hydroxyte‐trahydrofuran‐2‐one, which in turn could be obtained from L‐ascorbic acid.
Keywords:Typhonium giganteum Engl    natural product  cere-broside  chiron approach  synthesis
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