Synthesis of Amino-Dideoxy-Dl-Pentopyranoses and Their Ureido Derivatives

Abstract
Various 4-deoxy-α or β-erythro or threo-pentopyranoses aminated on position 1 [6 and 19]. 2 [38] or 3 [9, 22, 23, 24, 32 and 35] were synthesised from 2-methoxy-5,6-dihydro-2H-pyran [1] and methyl 2,3-anhydro-4-deoxy-α and β-DL-erythro-pentopyranoside [11]. Different reactions were investigated including azidation. cis-oxyamination, epimine formation and oxirane aminolysis. All these amino sugars were converted into their chloroethylureido derivatives.