197
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Oxetane δ‐Amino Acids: Chemoenzymatic Synthesis of 2,4‐Anhydro‐5‐N‐(t‐butoxycarbonyl)amino‐D‐lyxonic Acid

, , , &
Pages 187-196 | Received 24 Nov 2005, Accepted 07 Jan 2006, Published online: 17 Aug 2006

References

  • Graf von Roedern , E. and Kessler , H. 1994 . Eine Zuckeraminosäure als neuartiges Peptidmimetikum . Angew. Chem. , 106 ( 6 ) : 684 – 686 .
  • Gruner , S. A.W. , Locardi , E. , Lohof , E. and Kessler , H. 2002 . Carbohydrate‐based mimetics in drug design: sugar amino acids and carbohydrate scaffolds . Chem. Rev. , 102 : 491 – 514 .
  • Wessel , H. P. 2001 . “ Non‐sugar glycomimetics ” . In Glycoscience: Chemistry and Chemical Biology Edited by: Fraser‐Reid , B. , Tatsuta , K. and Thiem , K. Vol. III , 2725 – 2752 . Heidelberg : Springer Verlag .
  • Wessel , H. P. 2000 . “ Saccharide‐peptide hybrids ” . In Oligosaccharides in Chemistry and Biology: A Comprehensive Handbook. Synthesis of Oligosaccharides, Glycoconjugates and Glycomimetics, Part II: Synthesis of Oligosaccharide Mimetics Edited by: Ernst , B. , Hart , G. and Sinaÿ , P. Vol. I , 565 – 586 . Weinheim : Wiley/VCH .
  • Peri , F. , Cipolla , L. , Forni , E. and Nicotra , F. 2002 . Carbohydrate‐based scaffolds for the generation of sortiments of bioactive compounds . Monatshefte für Chemie , 133 ( 4 ) : 369 – 382 .
  • Chakraborty , T. K. , Jayaprakas , S. and Ghosh , S. 2002 . Sugar amino acid based scaffolds—novel peptidomimetics and their potential in combinatorial synthesis . Combinatorial Chem. High Throughput Screen. , 5 : 373 – 387 .
  • Edwards , A. A. , Ichihara , O. , Murfin , S. , Wilkes , R. , Whittaker , M. , Watkin , D. J. and Fleet , G. W.J. 2004 . Tetrahydrofuran‐based amino acids as library scaffolds . J. Comb. Chem. , 6 : 230 – 238 .
  • Matsuda , F. and Terashima , S. 1988 . Total synthesis of natural (+)‐sesbanimide A and (−)‐sesbanimide B1 . Tetrahedron , 44 ( 15 ) : 4721
  • Ning , J. and Kong , F. 1997 . Synthesis and glycosidic coupling reaction of substituted 2,6‐dioxabicyclo[3.1.0]hexanes: 1,2‐anhydro‐3,5‐di‐O‐benzyl‐α‐D‐ribofuranose . Carbohydr. Res. , 300 ( 4 ) : 355 – 360 .
  • Witty , D. R. , Fleet , G. W.J. , Vogt , K. , Wilson , F. X. , Wang , Y. , Storer , R. , Myers , P. L. and Wallis , C. J. 1990 . Ring contraction of 2‐O‐trifluoromethanesulphonates of α‐hydroxy‐γ‐lactones to oxetane carboxylic esters . Tetrahedron Lett. , 31 ( 33 ) : 4787 – 4790 .
  • Saksena , A. K. , Ganguly , A. K. , Girijavallabhan , V. M. , Pike , R. E. , Chen , Y.‐T. and Puar , M. S. 1992 . Ring contraction reactions of 2‐O‐methanesulfonates of α‐hydroxy‐γ‐lactones in aqueous medium to oxetane‐2‐carboxylic acids: a convenient synthesis of 3′‐O‐methyloxetanocin and a formal synthesis of oxetanocin . Tetrahedron Lett. , 33 ( 50 ) : 7721 – 7724 .
  • Jenkinson , S. F. , Harris , T. and Fleet , G. W.J. 2004 . Oxetane cis‐ and trans β‐amino‐acid scaffolds from D‐xylose by efficient SN2 reactions in oxetane rings: methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β‐amino‐acid . Tetrahedron Asymm. , 15 : 2667 – 2679 .
  • Wessel , H. P. and Ruiz , N. 1991 . α‐Glycosylation reactions with 2,3,4,6‐tetra‐O‐benzyl‐β‐D‐glucopyranosyl fluoride and triflic anhydride as promoter . J. Carbohydr. Chem. , 10 : 901 – 910 .
  • Günther , H. 1973 . NMR‐Spektroskopie 122 – 123 . Stuttgart : Georg Thieme Verlag .
  • Atta‐ur‐Rahman . 1986 . Nuclear Magnetic Resonance‐Basic Principles 85 – 86 . New York : Springer‐Verlag Inc. .
  • Bach , T. , Jödicke , K. , Kather , K. and Hecht , J. 1995 . Facial diastereoselectivity in the Paternò‐Büchi reaction of chiral silyl enol ethers . Angew. Chem., Int. Ed. , 34 : 2271 – 2273 .
  • Kotila , S. , Jäntti , A. , Penttinen , S. and Bach , T. 1996 . 3‐tert‐Butyl‐4‐methyl‐2‐phenyl‐3‐(tri‐methylsilyloxy)oxetane and 2‐(2‐benzyl‐oxyphenyl)‐3‐tert‐butyl‐3‐(trimethylsilyloxy)oxetane . Acta Cryst. , C52 : 1722 – 1725 .
  • Bach , T. , Jödicke , K. , Kather , K. and Fröhlich , R. 1997 . 1,3‐Allylic strain as a control element in the Paternò‐Büchi reaction of chiral silyl enol ethers: synthesis of diastereomerically pure oxetanes containing four contiguous stereogenic centers . J. Am. Chem. Soc. , 119 : 2437 – 2445 .
  • Barker , S. F. , Angus , D. , Taillefumier , C. , Probert , M. R. , Watkin , D. J. , Watterson , M. P. , Claridge , T. D.W. , Hungerford , N. L. and Fleet , G. W.J. 2001 . cis‐ and trans‐3‐Azido‐oxetane‐2‐carboxylate scaffolds: hexamers of oxetane cis‐β‐amino acids . Tetrahedron Lett. , 42 : 4247 – 4250 .
  • Suzuki , M. and Tomooka , K. 2004 . Anionic ring‐contraction reaction of cyclic acetal system: stereoselective approach to multi‐functionalized oxetanes . Synlett , 4 : 651 – 654 .
  • Gais , H‐J. , Jungen , M. and Vasudev , J. 2001 . Activation of pig liver esterase in organic media with organic polymers. Application to the enantioselective acylation of racemic functionalized secondary alcohols . J. Org. Chem. , 66 ( 10 ) : 3384 – 3396 .

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.