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Novel synthesis of carbohydrate fused alpha-amino gamma-lactams and glycopeptides by NIS mediated ring opening of donor-acceptor substituted cyclopropanes

Kishore, Gade and Gautam, Vibha and Chandrasekaran, Srinivasan (2014) Novel synthesis of carbohydrate fused alpha-amino gamma-lactams and glycopeptides by NIS mediated ring opening of donor-acceptor substituted cyclopropanes. In: CARBOHYDRATE RESEARCH, 390 . pp. 1-8.

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Official URL: http://dx.doi.org/10.1016/j.carres.2014.02.022

Abstract

alpha-Amino gamma-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused alpha-amino gamma-lactam and gamma-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: copyright for this article belongs to ELSEVIER SCI LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLAND
Keywords: Donor-acceptor cyclopropane; Ring opening; gamma-Lactam; Glycopeptide; N-Iodosuccinimide; Reductive cyclization
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 09 Jun 2014 09:51
Last Modified: 09 Jun 2014 09:51
URI: http://eprints.iisc.ac.in/id/eprint/49210

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