Synthesis of the Oligosaccharide Moieties of Musettamycin, Marcellomycin and Aclacinomycin A, Antitumor Antibiotics
作者:
Claude Monneret,
Alain Martin,
Mary Pais,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1988)
卷期:
Volume 7,
issue 2
页码: 417-434
ISSN:0732-8303
年代: 1988
DOI:10.1080/07328308808058934
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Condensation of benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (5) with 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide (10) carried out under Koenigs-Knorr conditions gave12. Total deprotection of12and N-dimethylation at C-3 led to17while selective removal of the 4-O-acetyl group led to13, a synthetic intermediate for preparing24and33. Condensation of13with di-O-acetyl-L-fucal (18) or 4-O-acetyl-L-amicetal (25) in the presence ofN-iodosuccinimide followed by hydrogenolysis of the C-2-I bond gave20and27respectively. The trisaccharide24then was obtained from20by the same sequence of reactions used to convert12into17. After deacetylation and oxidation, this set of reactions also transformed27into33.
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