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A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.
J Am Chem Soc. 2003 Oct 15; 125(41):12406-7.JA

Abstract

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.

Authors+Show Affiliations

Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14531673

Citation

Babu, Ravula Satheesh, and George A. O'Doherty. "A Palladium-catalyzed Glycosylation Reaction: the De Novo Synthesis of Natural and Unnatural Glycosides." Journal of the American Chemical Society, vol. 125, no. 41, 2003, pp. 12406-7.
Babu RS, O'Doherty GA. A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. J Am Chem Soc. 2003;125(41):12406-7.
Babu, R. S., & O'Doherty, G. A. (2003). A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. Journal of the American Chemical Society, 125(41), 12406-7.
Babu RS, O'Doherty GA. A Palladium-catalyzed Glycosylation Reaction: the De Novo Synthesis of Natural and Unnatural Glycosides. J Am Chem Soc. 2003 Oct 15;125(41):12406-7. PubMed PMID: 14531673.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides. AU - Babu,Ravula Satheesh, AU - O'Doherty,George A, PY - 2003/10/9/pubmed PY - 2003/12/16/medline PY - 2003/10/9/entrez SP - 12406 EP - 7 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 125 IS - 41 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/14531673/A_palladium_catalyzed_glycosylation_reaction:_the_de_novo_synthesis_of_natural_and_unnatural_glycosides_ L2 - https://dx.doi.org/10.1021/ja037097k DB - PRIME DP - Unbound Medicine ER -
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