Mechanistic studies of rearrangements during the ring expansions of cyclopropanated carbohydrates

Deuterium-labeling studies have been performed on the ring expansion of cyclopropanated carbohydrates. From these studies, mechanisms have been proposed for two unusual rearrangements. In addition, a selective deprotection of the 1,3-di-tert-butylsilyl ether protecting group at the secondary position versus the primary position has been observed. This is a high yielding transformation with the potential for general synthetic utility.