A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Research Abstract Details 

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A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Abstract Text:

Ravula Satheesh Babu,George A O'Doherty,

A highly stereoselective and sterospecific palladium-catalyzed glycosylation reaction of a variety of alcohols is reported. The reaction selectively converts alpha-2-substituted 6-carboxy-2H-pyran-3(6H)-ones into alpha-2-substituted 6-alkoxy-2H-pyran-3(6H)-ones with complete retention of configuration and similarly converts the pyranones with beta-carboxy groups into pyranones with beta-alkoxy groups. The reaction works equally well with both amino acid- and carbohydrate-based alcohols. To demonstrate the utility of this process for carbohydrate chemistry several of the products were selectively converted into alpha-manno-pyranosides in two additional steps. Because the 2-substituted 6-carboxy-2H-pyran-3(6H)-ones are prepared by asymmetric synthesis, this reaction can be used for the preparation of either d- or l-pyranones.

A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Publishing Authors By Initials

RS Babu,GA O'Doherty,

For similar heterocyclic compounds: heterocyclic compounds, 1-ring: pyrans research abstracts see: heterocyclic compounds: heterocyclic compounds, 1-ring: pyrans research

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A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 12406-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 15

MONTH: Oct

YEAR: 2003

A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Keywords Mesh Terms:

KEYWORDS: Pyrans

MESH TERMS: chemistry

Chemical & Substance for Abstract: A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Information

Substance Name: Palladium

Registry Number: 7440-05-3

Grant and Affiliation Information for A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

AFFILIATION: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: 1R01 GM63150-01A1

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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