Issue 4, 2015

Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues

Abstract

Glycosyl thiols are useful building blocks for the construction of compounds of biological and synthetic importance. Herein, we report a practical synthetic approach toward the efficient synthesis of glycosyl thiols via chemo- and regioselective S-deacetylation inspired by native chemical ligation. This strategy allows the large scale synthesis of glycosyl thiols by simple purification steps without column chromatography. In addition, deacetylation reagents (DTT) could also be recovered and regenerated by a simple process. Thiol containing taxol and artemisinin analogues were successfully prepared based on this methodology. Finally, auranofin, a glucose-based oral drug used to treat rheumatoid arthritis, was synthesized in concise steps and overall high yields.

Graphical abstract: Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues

Supplementary files

Article information

Article type
Paper
Submitted
15 Jan 2015
Accepted
12 Feb 2015
First published
16 Feb 2015

Green Chem., 2015,17, 2545-2551

Author version available

Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues

P. Shu, J. Zeng, J. Tao, Y. Zhao, G. Yao and Q. Wan, Green Chem., 2015, 17, 2545 DOI: 10.1039/C5GC00084J

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