1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation

Org Lett. 2006 Oct 12;8(21):4879-82. doi: 10.1021/ol061938l.

Abstract

[reaction: see text] The (1-naphthyl)propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely beta-selective.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Ethers / chemistry*
  • Glycosylation
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Ethers
  • Naphthalenes