Synthesis of D-glucose 3- and 6-[2-(perfluoroalkyl)ethyl] phosphates: a new type of anionic surfactant for biomedical use

Carbohydr Res. 1992 May 22;229(2):323-36. doi: 10.1016/s0008-6215(00)90578-0.

Abstract

D-Glucose 3- and 6-[sodium 2-(perfluoro-hexyl or -octyl)ethyl phosphates) have been synthesized by condensation of 1,2,3,4,-tetra-O-acetyl-beta-D-glucopyranose and 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose with 2-(perfluoroalkyl)ethylphosphoroditriazolides followed by O-deacetylation or deacetalation. The structures of the compounds were established on the basis of 1H-, 19F-, 31P-, and 13C-NMR data. These salts display strong surface activities and appear to have good biocompatibility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Blood Substitutes / chemical synthesis*
  • Blood Substitutes / chemistry
  • Fluorocarbons / chemistry*
  • Fluorocarbons / therapeutic use
  • Glucose / analogs & derivatives*
  • Glucose / chemistry*
  • Glucose / therapeutic use
  • Surface-Active Agents / chemical synthesis*
  • Surface-Active Agents / chemistry
  • Surface-Active Agents / therapeutic use

Substances

  • Biocompatible Materials
  • Blood Substitutes
  • Fluorocarbons
  • Surface-Active Agents
  • fluosol
  • Glucose