Affiliation:
1. Normandie Univ INSA Rouen UNIROUEN CNRS COBRA UMR 6014 76000 Rouen France
2. 24 Rue Lucien Tesnière 76130 Mont-Saint-Aignan France
Abstract
Abstract3‐Amino‐3‐deoxyglycosides constitute an essential class of nitrogen‐containing sugars. Among them, many important 3‐amino‐3‐deoxyglycosides possess a 1,2‐trans relationship. In view of their numerous biological applications, the synthesis of 3‐amino‐3‐deoxyglycosyl donors giving rise to a 1,2‐trans glycosidic linkage is thus an important challenge. Even though glycals are highly polyvalent donors, the synthesis and reactivity of 3‐amino‐3‐deoxyglycals have been little studied. In this work, we describe a new sequence, involving a Ferrier rearrangement and subsequent aza‐Wacker cyclization that allows the rapid synthesis of orthogonally protected 3‐amino‐3‐deoxyglycals. Finally a 3‐amino‐3‐deoxygalactal derivative was submitted for the first time to an epoxidation/glycosylation with high yield and great diastereoselectivity, highlighting FAWEG (Ferrier/Aza‐Wacker/Epoxidation/Glycosylation) as a new approach to access 1,2‐trans 3‐amino‐3‐deoxyglycosides.
Funder
Agence Nationale de la Recherche
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
1 articles.
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