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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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