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A Pd-catalyzed approach to (1-->6)-linked C-glycosides.
Org Lett. 2010 Sep 03; 12(17):3934-7.OL

Abstract

A flexible and robust method for the assembly of (1-->6)-linked C-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the alpha- or the beta-derivative, depending on the hydride source.

Authors+Show Affiliations

Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Gottingen, Tammannstr. 2, D-37077 Göttingen, Germany.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

20687593

Citation

Koester, Dennis C., et al. "A Pd-catalyzed Approach to (1-->6)-linked C-glycosides." Organic Letters, vol. 12, no. 17, 2010, pp. 3934-7.
Koester DC, Leibeling M, Neufeld R, et al. A Pd-catalyzed approach to (1-->6)-linked C-glycosides. Org Lett. 2010;12(17):3934-7.
Koester, D. C., Leibeling, M., Neufeld, R., & Werz, D. B. (2010). A Pd-catalyzed approach to (1-->6)-linked C-glycosides. Organic Letters, 12(17), 3934-7. https://doi.org/10.1021/ol101625p
Koester DC, et al. A Pd-catalyzed Approach to (1-->6)-linked C-glycosides. Org Lett. 2010 Sep 3;12(17):3934-7. PubMed PMID: 20687593.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A Pd-catalyzed approach to (1-->6)-linked C-glycosides. AU - Koester,Dennis C, AU - Leibeling,Markus, AU - Neufeld,Roman, AU - Werz,Daniel B, PY - 2010/8/7/entrez PY - 2010/8/7/pubmed PY - 2010/12/14/medline SP - 3934 EP - 7 JF - Organic letters JO - Org. Lett. VL - 12 IS - 17 N2 - A flexible and robust method for the assembly of (1-->6)-linked C-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the alpha- or the beta-derivative, depending on the hydride source. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20687593/A_Pd_catalyzed_approach_to__1__>6__linked_C_glycosides_ L2 - https://dx.doi.org/10.1021/ol101625p DB - PRIME DP - Unbound Medicine ER -