A highly stereoselective synthesis of 1-amino-2, 5-anhydro-1-deoxyhexitols via 2-trifluoromethyl-oxazolinium intermediates

JC Norrild, C Pedersen, I Søtofte

Index: Norrild, Jens Chr.; Pedersen, Christian; Sotofte, Inger Carbohydrate Research, 1997 , vol. 297, # 3 p. 261 - 272

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Citation Number: 5

Abstract

A series of 1-amino-2, 5-anhydro-1-deoxyalditols, namely derivatives of 1-amino-2, 5- anhydro-1-deoxy-d-glucitol,-d-mannitol and-d-talitol was prepared from the corresponding 1- deoxy-1-trifluoroacetamidohexitols by treatment with anhydrous hydrogen fluoride. The reaction was also performed on 1, 3-dideoxy-1-trifluoroacetamido-d-ribo-hexitol and 1- deoxy-1-trifluoroacetamido-l-rhamnitol which both gave the expected C-2 inverted ...