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Short and highly stereoselective total synthesis of d-ribo-configured ureido sugars

Ulgheri, Fausta and Giunta, Daniela and Spanu, Pietro (2008) Short and highly stereoselective total synthesis of d-ribo-configured ureido sugars. Tetrahedron, Vol. 64 (51), p. 11768-11775. ISSN 0040-4020. Article.

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DOI: 10.1016/j.tet.2008.09.080

Abstract

An highly stereoselective, flexible and very short synthetic approach to d-ribo-configured ureido monosaccharides of the aldose, aldonic acid and alditol series has been performed starting from the 5-(alditol-1-C-yl)-hydantoin intermediates, obtained via aldol-type addition reaction of hydantoin based building blocks to enantiomerically pure aldehydes. A study to assess the stereoselectivity of this reaction has been undertaken and a very high increase of diastereoselectivity was observed depending on the hydantoin protecting group. The imidazolidinone ring elaboration of 5-(alditol-1-C-yl)-hydantoin intermediates to give ureido sugar derivatives was studied.

Item Type:Article
ID Code:1382
Status:Published
Refereed:Yes
Uncontrolled Keywords:Ureido sugar derivatives, ureido monosaccharides, chemical synthesis
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Pergamon / Elsevier
ISSN:0040-4020
Copyright Holders:© 2008 Elsevier
Additional Information:Pubblicato online il 7 ottobre 2008.
Deposited On:18 Aug 2009 10:05

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