A short synthesis of D-glycero-D-manno-heptose 7-phosphate

Carbohydr Res. 2005 Dec 30;340(18):2808-11. doi: 10.1016/j.carres.2005.10.003. Epub 2005 Nov 2.


D-glycero-D-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses-has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the D-glycero-D-manno-configured derivative, which was separated from the L-glycero-L-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Heptoses / chemical synthesis*
  • Heptoses / chemistry
  • Molecular Structure
  • Pentoses / chemical synthesis
  • Pentoses / chemistry
  • Stereoisomerism
  • Sugar Phosphates / chemical synthesis*
  • Sugar Phosphates / chemistry


  • Bridged Bicyclo Compounds, Heterocyclic
  • Heptoses
  • Pentoses
  • Sugar Phosphates
  • benzyl 5,6-dideoxy-2,3-O-isopropylidene-lyxo-hept-5-enofuranoside
  • glycero-manno-heptopyranose 7-phosphate