Synthesis of Methyl 2,6-Dideoxy-3-C-Methyl-α-D-ribo- hexopyranoside (Methyl α-D-Mycaroside), a Component of the Antitomor Agent Mithramycin
作者:
RogerW. Binkley,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 2
页码: 227-242
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508058834
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Methyl α-D-mannopyranoside (4) was converted into methyl 2,6-dideoxy-3-C-methyl-ct-D-ribo-hexopyranoside (20) (methyl α-D-mycaroside) by an efficient sequence of reactions (Schemes 1 and 3). A similar set of reactions also was used to convert L-rhamnose (2) into methyl α-L-mycaroside (21). Attempted synthesis of methyl 2,6-diseoxy-3-C-methyl-a-D-arabino-hexopyranoside (22) (methyl α-D-olivomycosidej from methyl 6-deoxy-3-C-methyl-4-O-(2,2-dimethylpropanoyl)∼2-O-trif lyl-α-D-arabino-hexopyranoside (18), a compound generated during∼synthesis of 20, was thwarted by a methyl migration which produced methyl 2,6-dideoxy-2-C-methyl-α-D-ribo-hexopyranoside (23).
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