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

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.

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