Synthesis of nitrogen-functionalized beta-cycloaltrins.
We report the synthesis of functionalized beta-cycloaltrins 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-beta-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)-beta-cycloaltrin 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.
Casas-Solvas
Juan M
JM
Area de Química Orgánica, Universidad de Almería, 04120 Almería, Spain.
Ortega-Caballero
Fernando
F
Giménez-Martínez
Juan J
JJ
Vargas-Berenguel
Antonio
A
D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
D004852:Epoxy Compounds; D047392:beta-Cyclodextrins; D009584:Nitrogen