Journal article
2-Amino-2-Deoxytetrose Derivatives. 2. Preparation from d-Glyceraldehyde Acetonide: A Reinvestigation
Journal of carbohydrate chemistry, v 14(9), pp 1329-1341
01 Dec 1995
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
A diastereomeric mixture of nitriles 1a,b was prepared by a Strecker synthesis from D-glyceraldehyde acetonide and benzylamine. The reported selective hydrolysis of the acetonide group of 1a could not be accomplished. Nitrile diastereomers 1a,b were carried forward as a mixture to amines 3a,b where the diastereomers were readily separable. The hydrochloride of 3a was transformed via sequential debenzylation, N-acetylation, reduction, and exhaustive acetylation to the 2-amino-2-deoxy-D-threose derivatives 5 and 6. The corresponding 2-amino-2-deoxy-D-erythrose derivatives 10a and 11 were prepared similarly from amine 3b.
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Details
- Title
- 2-Amino-2-Deoxytetrose Derivatives. 2. Preparation from d-Glyceraldehyde Acetonide: A Reinvestigation
- Creators
- Peter A. Wade - Drexel UniversityStephen G. D'Ambrosio - Department of Chemistry , Drexel University
- Publication Details
- Journal of carbohydrate chemistry, v 14(9), pp 1329-1341
- Publisher
- Taylor & Francis Group
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- [Retired Faculty]
- Web of Science ID
- WOS:000202951600005
- Scopus ID
- 2-s2.0-21844482982
- Other Identifier
- 991019173630504721
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InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Web of Science research areas
- Biochemistry & Molecular Biology
- Chemistry, Organic