Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor

Zhitong Zheng; Liming Zhang

doi:10.1016/j.carres.2018.10.010

Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor

Carbohydr Res. 2019 Jan 1:471:56-63. doi: 10.1016/j.carres.2018.10.010. Epub 2018 Oct 26.

Authors

Zhitong Zheng¹, Liming Zhang²

Affiliations

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93117, United States.
² Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93117, United States. Electronic address: [email protected].

Abstract

A gold-catalyzed glucosylation method using an o-ethynylphenyl β-D-1-thioglucoside as donor is described. The reaction proceeds in a mostly S_N2 pathway. A series of α-D-glucosides are obtained in good yields and with up to 19:1 α-selectivity.

Keywords: 1,2-cis glycosidic bond; Glucosylation; Gold catalysis; S(N)2 pathway; o-ethynylphenyl β-D-1-thioglucoside.

MeSH terms

Carbohydrate Sequence
Catalysis
Glucosides / chemical synthesis*
Glucosides / chemistry
Glycosylation
Gold / chemistry*
Stereoisomerism
Substrate Specificity
Thioglucosides / chemistry*

Substances

Glucosides
Thioglucosides
Gold

Abstract

MeSH terms

Substances

Grants and funding