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A versatile and stereocontrolled route to pyranose and furanose C-glycosides.
Org Lett. 2004 Jul 22; 6(15):2611-4.OL

Abstract

[reaction: see text] 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.

Authors+Show Affiliations

Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. joanne.harvey@vuw.ac.nzNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

15255703

Citation

Harvey, Joanne E., et al. "A Versatile and Stereocontrolled Route to Pyranose and Furanose C-glycosides." Organic Letters, vol. 6, no. 15, 2004, pp. 2611-4.
Harvey JE, Raw SA, Taylor RJ. A versatile and stereocontrolled route to pyranose and furanose C-glycosides. Org Lett. 2004;6(15):2611-4.
Harvey, J. E., Raw, S. A., & Taylor, R. J. (2004). A versatile and stereocontrolled route to pyranose and furanose C-glycosides. Organic Letters, 6(15), 2611-4.
Harvey JE, Raw SA, Taylor RJ. A Versatile and Stereocontrolled Route to Pyranose and Furanose C-glycosides. Org Lett. 2004 Jul 22;6(15):2611-4. PubMed PMID: 15255703.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A versatile and stereocontrolled route to pyranose and furanose C-glycosides. AU - Harvey,Joanne E, AU - Raw,Steven A, AU - Taylor,Richard J K, PY - 2004/7/17/pubmed PY - 2005/2/11/medline PY - 2004/7/17/entrez SP - 2611 EP - 4 JF - Organic letters JO - Org. Lett. VL - 6 IS - 15 N2 - [reaction: see text] 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. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15255703/A_versatile_and_stereocontrolled_route_to_pyranose_and_furanose_C_glycosides_ L2 - https://dx.doi.org/10.1021/ol0490678 DB - PRIME DP - Unbound Medicine ER -