Ketone exchange in a sugar bisacetal

Richard S. Glass; Shuan Kwoh; Eugene P. Oliveto

doi:10.1016/S0008-6215(00)85034-X

Ketone exchange in a sugar bisacetal

Richard S. Glass, Shuan Kwoh, Eugene P. Oliveto

Chemistry and Biochemistry

Research output: Contribution to journal › Article

2 Scopus citations

Abstract

An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.

Original language	English (US)
Pages (from-to)	181-189
Number of pages	9
Journal	Carbohydrate Research
Volume	26
Issue number	1
DOIs	https://doi.org/10.1016/S0008-6215(00)85034-X
State	Published - Jan 1973

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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Glass, R. S., Kwoh, S., & Oliveto, E. P. (1973). Ketone exchange in a sugar bisacetal. Carbohydrate Research, 26(1), 181-189. https://doi.org/10.1016/S0008-6215(00)85034-X

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abstract = "An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.",

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AB - An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.

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