An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

Abstract

The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-β-D-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6-diallyl-β-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of β-cyclodextrin - not to mention (3) both the primary and secondary faces, simultaneously - in yields of up to 70%.