Abstract
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.
Acknowledgements
This paper is dedicated to Professor David R. Mootoo on the occasion of his 66th birthday. We are grateful to University of Michigan – Dearborn for supporting this research.
Disclosure statement
No potential conflict of interest was reported by the author(s).