Synthesis of amino-1, 4-anhydro-d-pentitols and amino-1, 5-anhydro-d-hexitols with the arabino configuration from (R)-glycidol

S Aragonès, F Bravo, Y Dı́az, MI Matheu…

Index: Aragones, Silvia; Bravo, Fernando; Diaz, Yolanda; Matheu, Ma. Isabel; Castillon, Sergio Tetrahedron Asymmetry, 2003 , vol. 14, # 13 p. 1847 - 1856

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Citation Number: 14

Abstract

2-Amino-1, 4-anhydro-pentitol and 3-amino-1, 5-anhydro-4-deoxy-hexitol with the arabino configuration were synthesised from (R)-glycidol using a metathesis reaction as the key step. The dihydrofuran or dihydropyran products obtained after the metathesis reaction were subjected to epoxidation, epoxide opening with azide anion and finally azide reduction.