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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

The Hetero Diels-Alder Approach to Carbohydrate-Containing Molecular Scaffolding

Author(s): Martina Cacciarini, Stefano Menichetti, Cristina Nativi and Barbara Richichi

Volume 4, Issue 1, 2007

Page: [47 - 57] Pages: 11

DOI: 10.2174/157017907779981570

Price: $65

Abstract

The hetero Diels-Alder reactions between α,α-dioxothiones, α-imino-α-oxothiones or orthothioquinones and glycals represent an effective way to prepare α- or β-, O- or N-glycosides with impressive chemo-, regio- and diastereoselectivity. The glycoderivatives so obtained are bicyclic, sulfur-containing, rigid structures, which, due to their differentiable functional groups, allow easy manipulations of the molecular architecture and can be used as veritable glycosyl scaffolds.

Keywords: Heteronuclear single quantum coherence, Neurokinin A, Chinese hamster ovary (CHO), Carbohydrate-containing scaffolds, NMR spectroscopy, matrix metalloelastase 12


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