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Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides.
Org Biomol Chem. 2009 Sep 21; 7(18):3855-61.OB

Abstract

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)(2) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag(2)CO(3) and Cu(OAc)(2) (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li HH
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, and School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing, 100191, China.
Ye XS
No affiliation info available

MeSH

CatalysisEthersGlycosidesGlycosylationHalogensIodinePalladiumStereoisomerismSubstrate Specificity

Pub Type(s)

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

Language

eng

PubMed ID

19707693

Citation

Li, Hou-Hua, and Xin-Shan Ye. "Regio- and Stereo-selective Synthesis of Aryl 2-deoxy-C-glycopyranosides By Palladium-catalyzed Heck Coupling Reactions of Glycals and Aryl Iodides." Organic & Biomolecular Chemistry, vol. 7, no. 18, 2009, pp. 3855-61.
Li HH, Ye XS. Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides. Org Biomol Chem. 2009;7(18):3855-61.
Li, H. H., & Ye, X. S. (2009). Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides. Organic & Biomolecular Chemistry, 7(18), 3855-61. https://doi.org/10.1039/b909248j
Li HH, Ye XS. Regio- and Stereo-selective Synthesis of Aryl 2-deoxy-C-glycopyranosides By Palladium-catalyzed Heck Coupling Reactions of Glycals and Aryl Iodides. Org Biomol Chem. 2009 Sep 21;7(18):3855-61. PubMed PMID: 19707693.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides. AU - Li,Hou-Hua, AU - Ye,Xin-Shan, Y1 - 2009/07/20/ PY - 2009/8/27/entrez PY - 2009/8/27/pubmed PY - 2009/11/6/medline SP - 3855 EP - 61 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 7 IS - 18 N2 - The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)(2) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag(2)CO(3) and Cu(OAc)(2) (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/19707693/Regio__and_stereo_selective_synthesis_of_aryl_2_deoxy_C_glycopyranosides_by_palladium_catalyzed_Heck_coupling_reactions_of_glycals_and_aryl_iodides_ L2 - https://doi.org/10.1039/b909248j DB - PRIME DP - Unbound Medicine ER -