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Efficient access to aminomannoside derivatives via formal [2+2] cycloaddition of triazolinediones and tri-O-acetyl-D-glucal


Dahl, R; Baldridge, K K; Finney, N S (2010). Efficient access to aminomannoside derivatives via formal [2+2] cycloaddition of triazolinediones and tri-O-acetyl-D-glucal. Synthesis, (13):2292-2296.

Abstract

Triazolinediones react with tri-O-acetyl-D-glucal to provide the corresponding diazetidines as single stereoisomers possessing the mannosamine configuration at C2. The diazetidines undergo facile ring opening with alcohol and amine nucleophiles. While this methodology is not fully developed, it is the first example of direct intermolecular conversion of a glycal to a mannosamine derivative. Computational analysis provides mechanistic insight that in turn leads to a proposal for the generation of glucosamine derivatives from glycals and triazolinediones.

Abstract

Triazolinediones react with tri-O-acetyl-D-glucal to provide the corresponding diazetidines as single stereoisomers possessing the mannosamine configuration at C2. The diazetidines undergo facile ring opening with alcohol and amine nucleophiles. While this methodology is not fully developed, it is the first example of direct intermolecular conversion of a glycal to a mannosamine derivative. Computational analysis provides mechanistic insight that in turn leads to a proposal for the generation of glucosamine derivatives from glycals and triazolinediones.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2010
Deposited On:18 Feb 2011 16:28
Last Modified:07 Dec 2017 06:32
Publisher:Thieme
ISSN:0039-7881
Additional Information:Special Issue
Publisher DOI:https://doi.org/10.1055/s-0029-1218803
Official URL:https://www.thieme-connect.com/ejournals/toc/synthesis/101560

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