Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties

Philip Redpath; Kerry A. Ness; Joanne Rousseau; Simon J. F. Macdonald; Marie E. Migaud

doi:10.1016/j.carres.2014.10.030

Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties

Philip Redpath
, Kerry A. Ness
, Joanne Rousseau
, Simon J. F. Macdonald
, Marie E. Migaud^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to thesynthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation ofthe glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series,we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalisedaromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of(±)-b-2-deoxy-glucose 6-phosphate.

Original language	English
Pages (from-to)	25-34
Number of pages	10
Journal	Carbohydrate Research
Volume	402
Early online date	11 Nov 2014
DOIs	https://doi.org/10.1016/j.carres.2014.10.030
Publication status	Published - 30 Jan 2015

Keywords

Tandem ene/intramolecular
Sakurai cyclisation
Transmetallation
C-Nucleoside
C-Glycoside
Glucose-6-phosphate bioisostere
NICOTINAMIDE RIBOSIDE
POLYSUBSTITUTED TETRAHYDROPYRANS
ANTIVIRAL EVALUATION
GENETIC SYSTEM
NUCLEOSIDES
ANALOGS
NAD(+)
CHEMISTRY
ROUTE
BASES

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10.1016/j.carres.2014.10.030

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title = "Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties",

abstract = "The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to thesynthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation ofthe glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series,we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalisedaromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of(±)-b-2-deoxy-glucose 6-phosphate.",

keywords = "Tandem ene/intramolecular, Sakurai cyclisation, Transmetallation, C-Nucleoside, C-Glycoside, Glucose-6-phosphate bioisostere, NICOTINAMIDE RIBOSIDE, POLYSUBSTITUTED TETRAHYDROPYRANS, ANTIVIRAL EVALUATION, GENETIC SYSTEM, NUCLEOSIDES, ANALOGS, NAD(+), CHEMISTRY, ROUTE, BASES",

author = "Philip Redpath and Ness, \{Kerry A.\} and Joanne Rousseau and Macdonald, \{Simon J. F.\} and Migaud, \{Marie E.\}",

year = "2015",

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day = "30",

doi = "10.1016/j.carres.2014.10.030",

language = "English",

volume = "402",

pages = "25--34",

journal = "Carbohydrate Research",

issn = "0008-6215",

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AU - Redpath, Philip

AU - Ness, Kerry A.

AU - Rousseau, Joanne

AU - Macdonald, Simon J. F.

AU - Migaud, Marie E.

PY - 2015/1/30

Y1 - 2015/1/30

N2 - The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to thesynthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation ofthe glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series,we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalisedaromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of(±)-b-2-deoxy-glucose 6-phosphate.

AB - The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to thesynthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation ofthe glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series,we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalisedaromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of(±)-b-2-deoxy-glucose 6-phosphate.

KW - Tandem ene/intramolecular

KW - Sakurai cyclisation

KW - Transmetallation

KW - C-Nucleoside

KW - C-Glycoside

KW - Glucose-6-phosphate bioisostere

KW - NICOTINAMIDE RIBOSIDE

KW - POLYSUBSTITUTED TETRAHYDROPYRANS

KW - ANTIVIRAL EVALUATION

KW - GENETIC SYSTEM

KW - NUCLEOSIDES

KW - ANALOGS

KW - NAD(+)

KW - CHEMISTRY

KW - ROUTE

KW - BASES

U2 - 10.1016/j.carres.2014.10.030

DO - 10.1016/j.carres.2014.10.030

M3 - Article

C2 - 25486220

SN - 0008-6215

VL - 402

SP - 25

EP - 34

JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties

Abstract

Keywords

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