Preparation of New Nucleoside Analogues from 3,6-Anhydrosugars¹

1. Presented at the 1st. International Meeting of the Portuguese Carbohydrate Chemistry Group, Lisbon, Portugal, September (1995).

Abstract

2-(3,6-Anhydro-2-deoxy-á-D-glucofuranosylamino)pyridine (2α), 1-N,3-N-(o-phenylene)-2-deoxy-α-D-allofuranosylamine (4) and 2-(2,5-anhydro-1-deoxy-D-arabino-pentitol-1-yl)benzimidazole (8) were synthesized by reaction of 2-aminopyridine or o-phenylenediamine with 3,6-anhydro-2-deoxy-D-glucose. Formation of compound (4) is explained through a Michael-type addition of the o-phenylenediamine on the intermediate α,β-unsaturated carbohydrate aldehyde (7).

1. Presented at the 1st. International Meeting of the Portuguese Carbohydrate Chemistry Group, Lisbon, Portugal, September (1995).

Notes

1. Presented at the 1st. International Meeting of the Portuguese Carbohydrate Chemistry Group, Lisbon, Portugal, September (1995).