2-Amino-2-Deoxytetrose Derivatives. 2. Preparation from d-Glyceraldehyde Acetonide: A Reinvestigation

Abstract

A diastereomeric mixture of nitriles 1a,b was prepared by a Strecker synthesis from D-glyceraldehyde acetonide and benzylamine. The reported selective hydrolysis of the acetonide group of 1a could not be accomplished. Nitrile diastereomers 1a,b were carried forward as a mixture to amines 3a,b where the diastereomers were readily separable. The hydrochloride of 3a was transformed via sequential debenzylation, N-acetylation, reduction, and exhaustive acetylation to the 2-amino-2-deoxy-D-threose derivatives 5 and 6. The corresponding 2-amino-2-deoxy-D-erythrose derivatives 10a and 11 were prepared similarly from amine 3b.     

ChemInform Abstract: Isomers of P2S2.

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