Reduction of sugar lactones to hemiacetals with lithium triethylborohydride

Carbohydr Res. 2016 Sep 2:432:17-22. doi: 10.1016/j.carres.2016.06.002. Epub 2016 Jun 11.

Abstract

Reduction of ribono-1,4-lactones and gulono-1,4-lactone as well as ribono-1,5-lactone and glucono-1,5-lactones with LTBH (1.2 equiv.) in CH2Cl2 at 0 °C for 30 min provided the corresponding pentose or hexose hemiacetals in high yields. Commonly used in carbohydrate chemistry protecting groups such as trityl, benzyl, silyl, acetals and to some extent acyls are compatible with this reduction.

Keywords: Hemiacetals; Lithium triethylborohydride; Reduction; Sugar lactols; Sugar lactones; Super-hydride.

MeSH terms

  • Acetals / chemical synthesis*
  • Acetals / chemistry
  • Borohydrides / chemistry
  • Gluconates / chemistry*
  • Lactones / chemistry*
  • Lithium / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Ribose / analogs & derivatives*
  • Ribose / chemistry

Substances

  • Acetals
  • Borohydrides
  • Gluconates
  • Lactones
  • ribonolactone
  • Ribose
  • Lithium
  • beta-glucono-1,5-lactone