115
Views
0
CrossRef citations to date
0
Altmetric
Preliminary Communication

Difluoromethylenated Polyhydroxylated Pyrrolidines: Facile Synthesis, Crystal Structure and Biological Evaluation

, , , &
Pages 991-997 | Published online: 19 Aug 2009

Bibliography

  • Butters TD , DwekRA, PlattFM. Inhibition of glycosphingolipid biosynthesis: application to lysosomal storage disorders.Chem. Rev.100, 4683–4696 (2000).
  • Sears P , WongCH. Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition.Angew. Chem. Int. Ed.38, 2301–2324 (1999).
  • Legler G . In: Iminosugars as Glycosidase Inhibitors. Stutz AE (Ed.). Wiley-VCH, Weinheim, Germany (1999).
  • Wrodnigg TM . From lianas to glycobiology tools: twenty-five years of 2,5-dideoxy-2,5-imino-D-mannitol. Monatsh Chem.133, 393–426 (2002).
  • Butters TD , van den BroekLAGM, FleetGWJet al. Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis. Tetrahedron Asymmetry.11, 113–124 (2000).
  • van den Broek LAGM , VermaasDJ, van Kemenade FJ et al. Synthesis of oxygen-substituted N-alkyl 1-deoxynojirimycin derivatives: aza sugar α-glucosidase inhibitors showing antiviral (HIV-1) and immunosuppressive activity. Rec. Trav. Chim. Pays-Bas.113, 507–516 (1994).
  • Arnone A , BravoP, DonadelliAet al. Asymmetric synthesis of fluorinated analogues of 1-deoxynojirimycin. J. Chem. Soc. Chem. Commun. 984–986 (1993).
  • Kajimoto T , LiuKKC, PedersonRLet al. Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation and modelling of glycosidase inhibitors. J. Am. Chem. Soc. 113, 6187–6196 (1991).
  • Butters TD , DwekRA, PlattFM. Therapeutic applications of imino sugars in lysosomal storage disorders.Curr. Top. Med. Chem.3, 561–574 (2003).
  • Yu CY , AsanoN, IkedaKet al. Looking glass inhibitors: L-DMDP, a more potent and specific inhibitor of α-glucosidases than the enantiomeric natural product DMDP. Chem. Commun. 17, 1936–1937 (2004).
  • Asano N , IkedaK, YuLet al. The L-enantiomers of DOO-sugar-mimicking iminosugars are noncompetitive inhibitors of D-glycohydrolase?. Tetrahedron Asymmetry 16, 223–229 (2005).
  • Garcia-Moreno MI , AguilarM, MelletCOet al. Intramolecular benzyl protection delivery: a practical synthesis of DMAP and DGDP from D-fructose. Org. Lett. 8, 297–299 (2006).
  • Wang RW , QiuXL, BolsM, Ortega-CaballeroF, QingFL. Synthesis and biological evaluation of glycosidase inhibitors: gem-difluoromethylenated nojirimycin analogues. J. Med. Chem.49, 2989–2997 (2006).
  • Zhang X , XiaH, DongX, JinJ, MengWD, QingFL. 3-deoxy-3,3-difluoro-D-arabinofuranose: first stereoselective synthesis and application in preparation of gem-difluorinated sugar nucleosides. J. Org. Chem.68, 9026–9033 (2003).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.