A versatile and stereocontrolled route to pyranose and furanose C-glycosides

J E  Harvey; S A  Raw; R J K  Taylor

doi:10.1021/ol0490678

A versatile and stereocontrolled route to pyranose and furanose C-glycosides

J E Harvey, S A Raw, R J K Taylor

Chemistry

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

Abstract

The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

Original language	English
Pages (from-to)	2611-2614
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	15
DOIs	https://doi.org/10.1021/ol0490678
Publication status	Published - 22 Jul 2004

Keywords

RAMBERG-BACKLUND APPROACH
LINKED DISACCHARIDES
CYCLIC ETHERS
AMINO-ACIDS
CHEMISTRY
RING
NUCLEOSIDES
TETRAHYDROPYRANS
CONSTRUCTION
CYCLIZATION

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10.1021/ol0490678

Cite this

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title = "A versatile and stereocontrolled route to pyranose and furanose C-glycosides",

abstract = "The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.",

keywords = "RAMBERG-BACKLUND APPROACH, LINKED DISACCHARIDES, CYCLIC ETHERS, AMINO-ACIDS, CHEMISTRY, RING, NUCLEOSIDES, TETRAHYDROPYRANS, CONSTRUCTION, CYCLIZATION",

author = "Harvey, {J E} and Raw, {S A} and Taylor, {R J K}",

year = "2004",

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journal = "Organic Letters",

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TY - JOUR

T1 - A versatile and stereocontrolled route to pyranose and furanose C-glycosides

AU - Harvey, J E

AU - Raw, S A

AU - Taylor, R J K

PY - 2004/7/22

Y1 - 2004/7/22

N2 - The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

AB - The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

KW - RAMBERG-BACKLUND APPROACH

KW - LINKED DISACCHARIDES

KW - CYCLIC ETHERS

KW - AMINO-ACIDS

KW - CHEMISTRY

KW - RING

KW - NUCLEOSIDES

KW - TETRAHYDROPYRANS

KW - CONSTRUCTION

KW - CYCLIZATION

U2 - 10.1021/ol0490678

DO - 10.1021/ol0490678

M3 - Article

SN - 1523-7060

VL - 6

SP - 2611

EP - 2614

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -