Application of 1′,2,3,3′,4,4′-Hexa-O-benzylsucrose in the Preparation of Sucrose Macrocycles via a Click Chemistry Route: Regioselectivity Study

Abstract

1′,2,3,3′,4,4′-Hexa-O-benzyl-sucrose was applied in the preparation of sucrose-based macrocycles via a click chemistry route. This was realized by protection of the 6′‒OH with silyl block followed by elongation of the glucose end with the ‒CH₂CH₂N₃ unit. Removal of the silyl block and subsequent propargylation of the released C6′‒OH afforded the corresponding synthon, cyclization of which under the click condition provided the desired macrocycle with the expected 1,4-pattern of substituents at the triazole ring.

Keywords:

• Click chemistry
• cyclization
• macrocycles
• sucrose

ACKNOWLEDGMENT

The support from Grant: POIG.01.01.02-14-102/09 (part-financed by the European Union within the European Regional Development Fund) is acknowledged.