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

[ Vol. 4 , Issue. 1 ]

Author(s):

Martina Cacciarini, Stefano Menichetti, Cristina Nativi and Barbara Richichi   Pages 47 - 57 ( 11 )

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

Affiliation:

Dipartimento di Chimica Organica “Ugo Schiff”, Universita' di Firenze, via della Lastruccia, 13 I-50019 Sesto Fiorentino (FI), Italy.



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