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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