L-fucose from vitamin C with only acetonide protection

Org Lett. 2014 Nov 7;16(21):5663-5. doi: 10.1021/ol502733x. Epub 2014 Oct 13.

Abstract

Addition of human milk oligosaccharides (HMO) to baby foods may protect infants from disease. As many simple HMOs are fucosylated this is likely to increase the demand for L-fucose as a synthetic building block. Any chemical synthesis must be cheap to compete with a biotechnological process. Acetonide is the only protecting group we have used in this new synthesis of L-fucose from vitamin C in 27% overall yield (purification by recrystallization; no chromatography required in the entire sequence).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascorbic Acid / chemistry*
  • Fucose / chemical synthesis
  • Fucose / chemistry*
  • Humans
  • Infant
  • Milk, Human / chemistry*
  • Molecular Structure
  • Oligosaccharides / chemistry*

Substances

  • Oligosaccharides
  • Fucose
  • Ascorbic Acid