Diisobutylaluminium hydride (DIBAL-H) is promoting a selective clockwise debenzylation of perbenzylated 6A,6D-dideoxy-α-cyclodextrin

A novel C2 symmetric cyclodextrin (CD) was obtained possessing three pairs of functionalities on its primary rim. Its synthesis relies on a first generation diisobutylaluminium hydride (DIBAL-H) induced 6A,6D-de-O-benzylation of a perbenzylated CD followed by a second generation 6C,6F-de-O-benzylation on a resulting perbenzylated 6A,6D-dideoxy-CD conceived to undergo a regioselective clockwise reaction.