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De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis.
J Am Chem Soc. 2003 Jul 23; 125(29):8714-5.JA

Abstract

A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.

Authors+Show Affiliations

Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

12862452

Citation

Comely, Alex C., et al. "De Novo Asymmetric Bio- and Chemocatalytic Synthesis of Saccharides - Stereoselective Formal O-glycoside Bond Formation Using Palladium Catalysis." Journal of the American Chemical Society, vol. 125, no. 29, 2003, pp. 8714-5.
Comely AC, Eelkema R, Minnaard AJ, et al. De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis. J Am Chem Soc. 2003;125(29):8714-5.
Comely, A. C., Eelkema, R., Minnaard, A. J., & Feringa, B. L. (2003). De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis. Journal of the American Chemical Society, 125(29), 8714-5.
Comely AC, et al. De Novo Asymmetric Bio- and Chemocatalytic Synthesis of Saccharides - Stereoselective Formal O-glycoside Bond Formation Using Palladium Catalysis. J Am Chem Soc. 2003 Jul 23;125(29):8714-5. PubMed PMID: 12862452.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis. AU - Comely,Alex C, AU - Eelkema,Rienk, AU - Minnaard,Adriaan J, AU - Feringa,Ben L, PY - 2003/7/17/pubmed PY - 2003/9/13/medline PY - 2003/7/17/entrez SP - 8714 EP - 5 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 125 IS - 29 N2 - A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12862452/De_novo_asymmetric_bio__and_chemocatalytic_synthesis_of_saccharides___stereoselective_formal_O_glycoside_bond_formation_using_palladium_catalysis_ L2 - https://dx.doi.org/10.1021/ja0347538 DB - PRIME DP - Unbound Medicine ER -