A new route to exo-glycals using the Ramberg-Backlund rearrangement

F K  Griffin; D E  Paterson; P V  Murphy; R J K  Taylor

A new route to exo-glycals using the Ramberg-Backlund rearrangement

F K Griffin, D E Paterson, P V Murphy, R J K Taylor

Chemistry

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

Abstract

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Backlund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Original language	English
Pages (from-to)	1305-1322
Number of pages	18
Journal	European Journal of Organic Chemistry
Issue number	7
Publication status	Published - Apr 2002

Keywords

carbohydrates
sulfones
rearrangements
enol ethers
BETA-D-GALACTOSIDASE
WITTIG OLEFINATION
C-GLYCOSIDES
1-THIOGLYCOSIDES
THIOGLYCOSIDES
DERIVATIVES
LACTONES

Cite this

@article{543ced6c75e64bb182526c5ccc98360b,

title = "A new route to exo-glycals using the Ramberg-Backlund rearrangement",

abstract = "A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Backlund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).",

keywords = "carbohydrates, sulfones, rearrangements, enol ethers, BETA-D-GALACTOSIDASE, WITTIG OLEFINATION, C-GLYCOSIDES, 1-THIOGLYCOSIDES, THIOGLYCOSIDES, DERIVATIVES, LACTONES",

author = "Griffin, {F K} and Paterson, {D E} and Murphy, {P V} and Taylor, {R J K}",

year = "2002",

month = apr,

language = "English",

pages = "1305--1322",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley-Blackwell",

number = "7",

}

TY - JOUR

T1 - A new route to exo-glycals using the Ramberg-Backlund rearrangement

AU - Griffin, F K

AU - Paterson, D E

AU - Murphy, P V

AU - Taylor, R J K

PY - 2002/4

Y1 - 2002/4

N2 - A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Backlund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

AB - A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Backlund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

KW - carbohydrates

KW - sulfones

KW - rearrangements

KW - enol ethers

KW - BETA-D-GALACTOSIDASE

KW - WITTIG OLEFINATION

KW - C-GLYCOSIDES

KW - 1-THIOGLYCOSIDES

KW - THIOGLYCOSIDES

KW - DERIVATIVES

KW - LACTONES

M3 - Article

SN - 1099-0690

SP - 1305

EP - 1322

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -