Pseudo-sugars. VII. Synthesis of Pseudo-hexopyranose Derivatives with α- and β-Gluco Configurations

Several derivatives of pseudo-hexopyranose (5-hydroxymethyl-1,2,3,4-cyclohexanetetrol) with α-gluco, (1,2,4/3,5), and β-gluco, (1,3,5/2,4), configurations were synthesized starting from the compounds obtained by cis-hydroxylation and oxyamination of Dl-di-O-acetyl-(1,3/2)-3-bromomethyl-5-cyclohexene-1,2-diol. The 1H NMR chemical shifts of the acetyl methyl protons of the several acetyl derivatives of N-(p-tolylsulfonyl)-pseudoglucosamines are discussed.