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

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

Journal Name: Current Organic Synthesis

Volume 4 , Issue 1 , 2007

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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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Article Details

VOLUME: 4
ISSUE: 1
Year: 2007
Page: [47 - 57]
Pages: 11
DOI: 10.2174/157017907779981570

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