Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

Sajal Kumar Maity; Nabamita Basu; Rina Ghosh

doi:10.1016/j.carres.2012.03.024

Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

Carbohydr Res. 2012 Jun 1:354:40-8. doi: 10.1016/j.carres.2012.03.024. Epub 2012 Apr 7.

Authors

Sajal Kumar Maity¹, Nabamita Basu, Rina Ghosh

Affiliation

¹ Department of Chemistry, Jadavpur University, Kolkata 700 032, India.

PMID: 22542575
DOI: 10.1016/j.carres.2012.03.024

Abstract

N-(p-Methylphenylthio)-ε-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both 'armed' and 'disarmed' thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy.

Publication types

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

MeSH terms

Mesylates / chemical synthesis
Mesylates / chemistry*
Molecular Structure
Thioglycosides / chemistry*
Trimethylsilyl Compounds / chemical synthesis
Trimethylsilyl Compounds / chemistry*

Substances

Mesylates
Thioglycosides
Trimethylsilyl Compounds
trimethylsilyl trifluoromethanesulfonate