Cyclopropylmethylidene as a versatile protecting group for carbohydrate synthesis.

Cyclopropylmethylidene has been developed as a versatile protecting group for carbohydrate synthesis. It can be formed by acid-catalyzed acetalization between cyclopropanecarboxaldehyde and 1,3-diols of sugar molecules. Selective reductive opening of the 4,6-O-cyclopropylmethylidene can be achieved to afford a C4 free hydroxyl group and a C6-cyclopropylmethyl (CPM) ether or vice versa. The cyclopropylmethylidene was found to be less stable than benzylidene under acidic conditions. [ABSTRACT FROM AUTHOR]