Cyclopropylmethylidene as a versatile protecting group for carbohydrate synthesis

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.

Graphical Abstract

Keywords:

• Cyclopropylmethylidene
• protecting group
• 1,3-diol
• carbohydrate

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).