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

Research output: Contribution to journal › Article › peer-review

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
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/S0008-6215(00)85034-X

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title = "Ketone exchange in a sugar bisacetal",

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.",

author = "Glass, \{Richard S.\} and Shuan Kwoh and Oliveto, \{Eugene P.\}",

year = "1973",

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doi = "10.1016/S0008-6215(00)85034-X",

language = "English (US)",

volume = "26",

pages = "181--189",

journal = "Carbohydrate Research",

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T1 - Ketone exchange in a sugar bisacetal

AU - Glass, Richard S.

AU - Kwoh, Shuan

AU - Oliveto, Eugene P.

PY - 1973/1

Y1 - 1973/1

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/49549171244

UR - https://www.scopus.com/pages/publications/49549171244#tab=citedBy

U2 - 10.1016/S0008-6215(00)85034-X

DO - 10.1016/S0008-6215(00)85034-X

M3 - Article

AN - SCOPUS:49549171244

SN - 0008-6215

VL - 26

SP - 181

EP - 189

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 1

ER -

Ketone exchange in a sugar bisacetal

Abstract

ASJC Scopus subject areas

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