Intramolecular benzyl protection delivery: a practical synthesis of DMDP and DGDP from D-fructose

Org Lett. 2006 Jan 19;8(2):297-9. doi: 10.1021/ol052668u.

Abstract

[reaction: see text] A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Ethers, Cyclic / chemical synthesis
  • Fructose / analogs & derivatives
  • Fructose / chemistry*
  • Glycoside Hydrolases / antagonists & inhibitors
  • Imino Pyranoses / chemical synthesis
  • Imino Pyranoses / chemistry
  • Imino Pyranoses / pharmacology
  • Mannitol / analogs & derivatives*
  • Mannitol / chemical synthesis
  • Mannitol / chemistry
  • Mannitol / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Sorbitol / analogs & derivatives*
  • Sorbitol / chemical synthesis
  • Sorbitol / chemistry
  • Sorbitol / pharmacology
  • Stereoisomerism

Substances

  • 2,5-dideoxy-2,5-imino-D-glucitol
  • 2,5-dideoxy-2,5-imino-D-mannitol
  • Ethers, Cyclic
  • Imino Pyranoses
  • Fructose
  • Mannitol
  • Sorbitol
  • Glycoside Hydrolases