Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose

Laetitia den Drijver; Cedric W. Holzapfel; Johannes M. Koekemoer; Gert J. Kruger; Martha S. van Dyk

doi:10.1016/S0008-6215(00)90140-X

Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose

Laetitia den Drijver
, Cedric W. Holzapfel
, Johannes M. Koekemoer
, Gert J. Kruger
, Martha S. van Dyk

Chemical Sciences

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

7 Citations (Scopus)

Abstract

Stannylation of 2,3-O-isopropylidene-β-d-fructopyranose with dibutyltin oxide followed by brominolysis afforded 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulopyranose, which was characterised as its oxime. Brominolysis of the O-dibutylstannylene derivative of 1,2-O-isopylidene-β-d-fructopyranose furnished 1,2-O-isopropylidene-β-d-threo-hexo-2,5-diulopyranose, which was characterised as the corresponding O-methyloxime diacetate.

Original language	English
Pages (from-to)	141-150
Number of pages	10
Journal	Carbohydrate Research
Volume	155
Issue number	C
DOIs	https://doi.org/10.1016/S0008-6215(00)90140-X
Publication status	Published - 1 Nov 1986

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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@article{0649e9f0ef1f41c196b53dad00f8b0bd,

title = "Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose",

abstract = "Stannylation of 2,3-O-isopropylidene-β-d-fructopyranose with dibutyltin oxide followed by brominolysis afforded 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulopyranose, which was characterised as its oxime. Brominolysis of the O-dibutylstannylene derivative of 1,2-O-isopylidene-β-d-fructopyranose furnished 1,2-O-isopropylidene-β-d-threo-hexo-2,5-diulopyranose, which was characterised as the corresponding O-methyloxime diacetate.",

author = "\{den Drijver\}, Laetitia and Holzapfel, \{Cedric W.\} and Koekemoer, \{Johannes M.\} and Kruger, \{Gert J.\} and \{van Dyk\}, \{Martha S.\}",

year = "1986",

month = nov,

day = "1",

doi = "10.1016/S0008-6215(00)90140-X",

language = "English",

volume = "155",

pages = "141--150",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd.",

number = "C",

}

Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose. / den Drijver, Laetitia; Holzapfel, Cedric W.; Koekemoer, Johannes M. et al.
In: Carbohydrate Research, Vol. 155, No. C, 01.11.1986, p. 141-150.

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

TY - JOUR

T1 - Regioselective oxidation of carbohydrate triols

T2 - facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose

AU - den Drijver, Laetitia

AU - Holzapfel, Cedric W.

AU - Koekemoer, Johannes M.

AU - Kruger, Gert J.

AU - van Dyk, Martha S.

PY - 1986/11/1

Y1 - 1986/11/1

N2 - Stannylation of 2,3-O-isopropylidene-β-d-fructopyranose with dibutyltin oxide followed by brominolysis afforded 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulopyranose, which was characterised as its oxime. Brominolysis of the O-dibutylstannylene derivative of 1,2-O-isopylidene-β-d-fructopyranose furnished 1,2-O-isopropylidene-β-d-threo-hexo-2,5-diulopyranose, which was characterised as the corresponding O-methyloxime diacetate.

AB - Stannylation of 2,3-O-isopropylidene-β-d-fructopyranose with dibutyltin oxide followed by brominolysis afforded 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulopyranose, which was characterised as its oxime. Brominolysis of the O-dibutylstannylene derivative of 1,2-O-isopylidene-β-d-fructopyranose furnished 1,2-O-isopropylidene-β-d-threo-hexo-2,5-diulopyranose, which was characterised as the corresponding O-methyloxime diacetate.

UR - https://www.scopus.com/pages/publications/37949043024

U2 - 10.1016/S0008-6215(00)90140-X

DO - 10.1016/S0008-6215(00)90140-X

M3 - Article

AN - SCOPUS:37949043024

SN - 0008-6215

VL - 155

SP - 141

EP - 150

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - C

ER -

Regioselective oxidation of carbohydrate triols: facile synthesis of 2,3-O-isopropylidene-β-d-threo-hexo-2,4-diulo-pyranose and 1,2-O-isopropylidene-β-d-threo-hexo-2,5,diulo-pyranose

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