285
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

The Synthesis of a New Class of Potential Inhibitors for Glycoside HydrolasesFootnote

&
Pages 529-547 | Received 07 Feb 2005, Accepted 06 Apr 2005, Published online: 16 Aug 2006

References

  • Asano , N. 2003 . Glycosidase inhibitors: update and perspectives on practical use . Glycobiology , 13 : 93R – 104R .
  • Stick , R. V. and Watts , A. G. 2002 . The chameleon of retaining glycoside hydrolases and retaining glycosyl transferases: the catalytic nucleophile . Monatsh. Chem. , 133 : 541 – 554 .
  • Blüchel , C. , Ramana , C. V. and Vasella , A. 2003 . Synthesis of monosaccharide‐derived spirocyclic cyclopropylamines and their evaluation as glycosidase inhibitors . Helv. Chim. Acta , 86 : 2998 – 3036 .
  • Vaghefi , M. M. , Bernacki , R. J. , Dalley , N. K. , Wilson , B. E. and Robins , R. K. 1987 . Synthesis of glycopyranosylphosphonate analogs of certain natural nucleoside diphosphate sugars as potential inhibitors of glycosyltransferases . J. Med. Chem. , 30 : 1383 – 1391 .
  • Overkleeft , H. S. , van Wiltenburg , J. and Pandit , U. K. 1994 . A facile transformation of sugar lactones to aza sugars . Tetrahedron , 50 : 4215 – 4224 .
  • Li , X. , Ohtake , H. , Takahashi , H. and Ikegami , S. 2001 . A facile synthesis of 1′‐C‐alkyl‐α‐disaccharides from 1‐C‐alkyl‐hexopyranoses and methyl 1‐C‐methyl‐hexopyranosides . Tetrahedron , 57 : 4297 – 4309 .
  • Shuto , S. , Yahiro , Y. , Ichikawa , S. and Matsuda , A. 2000 . Synthesis of 3,7‐anhydro‐D‐glycero‐Dido‐octitol 1,5,6‐trisphosphate as an IP3 receptor ligand using a radical cyclization reaction with a vinylsilyl tether as the key step. Conformational restriction strategy using steric repulsion between adjacent bulky protecting groups on a pyranose ring . J. Org. Chem. , 65 : 5547 – 5557 .
  • Timmers , C. M. , Leeuwenburgh , M. A. , Verheijen , J. C. , van der Marel , G. A. and van Boom , J. H. 1996 . Rhodium(II) catalyzed asymmetric cyclopropanation of glycals with ethyl diazoacetate . Tetrahedron: Asymmetry , 7 : 49 – 52 .
  • Henry , K. J. Jr. and Fraser‐Reid , B. 1995 . Cyclopropanation of glycals: application to the synthesis of 2‐deoxy‐2‐vinyl glycosides . Tetrahedron Lett. , 36 : 8901 – 8904 .
  • Chaudhary , S. K. and Hernandez , O. 1979 . A simplified procedure for the preparation of triphenylmethyl ethers . Tetrahedron Lett. , : 95 – 98 .
  • Bernet , B. and Vasella , A. 1979 . Carbocyclic compounds from monosaccharides. I. Transformations in the glucose series . Helv. Chim. Acta , 62 : 1990 – 2016 .
  • Aurrecoechea , J. M. , Lopez , B. and Arrate , M. 2000 . Synthesis of vinyl‐ and alkynylcyclopentanetetraols by SmI2/Pd(0)‐promoted carbohydrate ring‐contraction . J. Org. Chem. , 65 : 6493 – 6501 .
  • Stick , R. V. , Stubbs , K. A. , Tilbrook , D. M.G. and Watts , A. G. 2002 . A new catalyst for the reductive elimination of acylated glycosyl bromides to form glycals . Aust. J. Chem. , 55 : 83 – 85 .
  • Sudha , A. V.R.L. and Nagarajan , M. 1998 . Carbohydrates to carbocycles: an expedient synthesis of pseudo‐sugars . Chem. Commun. , : 925 – 926 .
  • Ogilvie , K. K. and Beaucage , S. L. 1979 . Fluoride ion promoted deprotection and transesterification in nucleotide triesters . Nucleic Acids Res. , 7 : 805 – 823 .
  • Atherton , F. R. , Openshaw , H. T. and Todd , A. R. 1945 . Phosphorylation. I. Dibenzyl chlorophosphonate as a phosphorylating agent . J. Chem. Soc. , : 382 – 385 .
  • Kelley , J. L. , McLean , E. W. , Crouch , R. C. , Averett , D. R. and Tuttle , J. V. 1995 . [[(Guaninylalkyl)phosphinico]methyl]phosphonic acids. Multisubstrate analog inhibitors of human erythrocyte purine nucleoside phosphorylase . J. Med. Chem. , 38 : 1005 – 1014 .
  • Ogilvie , K. K. , Beaucage , S. L. and Entwistle , D. W. 1976 . A facile method for the removal of phosphate protecting groups in nucleotide synthesis . Tetrahedron Lett. , : 1255 – 1256 .
  • Wallis , E. S. and Lane , J. F. 1946 . Hofmann reaction . Org. React. , : 267 – 306 .
  • McAuliffe , J. C. and Stick , R. V. 1997 . β‐Acarbose. I. The synthesis of 1‐epivalienamine . Aust. J. Chem. , 50 : 193 – 196 .

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.