Eight Stereoisomers of Homonojirimycin from d-Mannose

Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ

Synthesis from d‑Altrose of (5<i>R</i>,6<i>R</i>,7<i>R</i>,8<i>S</i>)‑5,7-Dihydroxy-8-hydroxymethylconidine and 2,4-Dideoxy-2,4-imino‑d‑glucitol, Azetidine Analogues of Swainsonine and 1,4-Dideoxy-1,4-imino‑d‑mannitol

Ring closure of a 3,5-di-<i>O</i>-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine