Synthesis of Nitrogen-Functionalized β-Cycloaltrins

摘要

We report the synthesis of functionalized β-cy-cloaltrins having azido groups at C-3, C-6, and both C-3 and C-6 by nucleophilic epoxy ring-opening of per-2,3-anhidro-β-cyclomannin derivatives. The value of these compounds as templates for further functionalization is exemplified by the conversion of heptakis(3,6-diazido-3,6-dideoxy)-β-cycloal-trin into the per-3,6-diamino, per-3,6-diacetamido, per-3,6-dichloroacetamido, and per[3,6-bis(N′-ethylureido)] derivatives in good yields.