Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Jun 6:122:154511.
doi: 10.1016/j.tetlet.2023.154511. Epub 2023 Apr 19.

Potassium carbonate-mediated β-selective anomeric O-alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids

Ishani Lakshika Hettiarachchi  1 , Fenglang Wu  1 , Maria Stoica  2 , Xiaohua Li  2 , Jianglong Zhu  1
Affiliations

Potassium carbonate-mediated β-selective anomeric O-alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids

Ishani Lakshika Hettiarachchi et al. Tetrahedron Lett. .

Abstract

Stereoselective construction of a variety of β-glycosides can be achieved using abundant and inexpensive K2CO3-mediated stereoselective anomeric O-alkylation of sugar lactols with primary electrophiles. In addition, application of this methodology to the synthesis of various azido-modified glycosphingolipids has been accomplished in good yields and excellent anomeric selectivity using sphingosine-derived primary triflate.

Keywords: Anomeric O-alkylation; Carbohydrates; Glycosphingolipids; Glycosylation.

PubMed Disclaimer

Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Scheme 1.
Scheme 1.
Synthesis of β-glycosides via stereoselective anomeric O-alkylation.
See this image and copyright information in PMC

References

    1. Varki A, Glycobiology 3 (1993) 97–130. - PMC - PubMed
    1. Toshima K, Tatsuta K, Chem. Rev 93 (1993) 1503–1531.
    1. Panza M, Pistorio SG, Stine KJ, Demchenko AV, Chem. Rev 118 (2018) 8105–8150. - PMC - PubMed
    1. Nielsen MM, Pedersen CM, Chem. Rev 118 (2018) 8285–8358. - PubMed
    1. Nigudkar SS, Demchenko AV, Chem. Sci 6 (2015) 2687–2704. - PMC - PubMed

LinkOut - more resources