Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation

Org Lett. 2010 Dec 17;12(24):5628-31. doi: 10.1021/ol1023079. Epub 2010 Nov 18.

Abstract

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in oligosaccharide synthesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemistry*
  • Glycosylation
  • Imidoesters / chemistry*
  • Molecular Structure
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alcohols
  • Imidoesters
  • Sulfhydryl Compounds
  • alkoxyl radical