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2-Amino-2-Deoxytetrose Derivatives. 2. Preparation fromd-Glyceraldehyde Acetonide: A Reinvestigation

 

作者: PeterA. Wade,   StephenG. D'Ambrosio,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1995)
卷期: Volume 14, issue 9  

页码: 1329-1341

 

ISSN:0732-8303

 

年代: 1995

 

DOI:10.1080/07328309508005414

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

A diastereomeric mixture of nitriles1a,bwas prepared by a Strecker synthesis from D-glyceraldehyde acetonide and benzylamine. The reported selective hydrolysis of the acetonide group of1acould not be accomplished. Nitrile diastereomers1a,bwere carried forward as a mixture to amines3a,bwhere the diastereomers were readily separable. The hydrochloride of3awas transformed via sequential debenzylation,N-acetylation, reduction, and exhaustive acetylation to the 2-amino-2-deoxy-D-threose derivatives5and6. The corresponding 2-amino-2-deoxy-D-erythrose derivatives10aand11were prepared similarly from amine3b.

 

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