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
Current Organic Synthesis
Title: The Hetero Diels-Alder Approach to Carbohydrate-Containing Molecular Scaffolding
Volume: 4 Issue: 1
Author(s): Martina Cacciarini, Stefano Menichetti, Cristina Nativi and Barbara Richichi
Affiliation:
Keywords: Heteronuclear single quantum coherence, Neurokinin A, Chinese hamster ovary (CHO), Carbohydrate-containing scaffolds, NMR spectroscopy, matrix metalloelastase 12
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.
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Cite this article as:
Cacciarini Martina, Menichetti Stefano, Nativi Cristina and Richichi Barbara, The Hetero Diels-Alder Approach to Carbohydrate-Containing Molecular Scaffolding, Current Organic Synthesis 2007; 4 (1) . https://dx.doi.org/10.2174/157017907779981570
DOI https://dx.doi.org/10.2174/157017907779981570 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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