NewN-Acylating Reagents Derived from 3-Deoxy-l-glycero-tetronic Acid1
作者:
Ping-sheng Lei,
Yuji Ogawa,
Pavol Kováč,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1996)
卷期:
Volume 15,
issue 4
页码: 485-500
ISSN:0732-8303
年代: 1996
DOI:10.1080/07328309608005668
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Commercially availableN-Boc-4-O-benzyl-l-homoserine was treated with trifluoroacetic acid and the corresponding,N-deprotected derivative was submitted to deamination to give 4-O-benzyl-3-deoxy-l-glycero-tetronic acid (5). In another approach to 3-deoxy-l-glycero-tetronic acid protected at position 4, the carboxylic groups in L-malic acid were reduced, and the resulting triol was benzylidenated. Oxidation of the 2,4-O-benzylidene derivative formed with CrO3-pyridine complex in the presence oft-butyl alcohol gavet-butyl 2,4-O-benzylidene-3-deoxy-l-glycero-tetronate (13). The latter was saponified with aqueous sodium hydroxide to give, after Na+exchange for H+, 2,4-O-benzylidene-3-deoxy-l-glycero-tetronic acid (15). Opening of the acetal ring in13, followed by hydrolytic cleavage of thet-butyl ester function gave material indistinguishable from5obtained in the original way. When tested for their efficiency ofN-acylation of derivatives of D-perosamine, both acids5and15gave the corresponding tetronamido derivatives in high yields.
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