A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

J S  HOULTON; W B  MOTHERWELL; B C  ROSS; M J  TOZER; D J  WILLIAMS; A M Z  SLAWIN

A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

J S HOULTON, W B MOTHERWELL, B C ROSS, M J TOZER, D J WILLIAMS, A M Z SLAWIN

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

Abstract

A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

Original language	English
Pages (from-to)	8087-8106
Number of pages	20
Journal	Tetrahedron
Volume	49
Issue number	36
Publication status	Published - 3 Sept 1993

Keywords

NUCLEOSIDES
INHIBITORS
FLUORINE

Cite this

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title = "A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES",

abstract = "A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.",

keywords = "NUCLEOSIDES, INHIBITORS, FLUORINE",

author = "HOULTON, {J S} and MOTHERWELL, {W B} and ROSS, {B C} and TOZER, {M J} and WILLIAMS, {D J} and SLAWIN, {A M Z}",

year = "1993",

month = sep,

day = "3",

language = "English",

volume = "49",

pages = "8087--8106",

journal = "Tetrahedron",

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T1 - A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

AU - HOULTON, J S

AU - MOTHERWELL, W B

AU - ROSS, B C

AU - TOZER, M J

AU - WILLIAMS, D J

AU - SLAWIN, A M Z

PY - 1993/9/3

Y1 - 1993/9/3

N2 - A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

AB - A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

KW - NUCLEOSIDES

KW - INHIBITORS

KW - FLUORINE

M3 - Article

SN - 0040-4020

VL - 49

SP - 8087

EP - 8106

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

Abstract

Keywords

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