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Original Articles

Synthesis of N‐Protected Galactosamine Building Blocks from d‐Tagatose via the Heyns Rearrangement

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Pages 33-41 | Received 22 Aug 2005, Accepted 20 Oct 2005, Published online: 21 Aug 2006

References

  • Varki , A. , Cummings , R. , Esko , J. , Freeze , H. , Hart , G. and Marth , J. 1999 . Essential of Glycobiology New York : Cold Spring Harbor Laboratory Press .
  • Kolter , T. and Sandhoff , K. 1999 . The glycospingolipidoses. From diseases to basic principles of metabolism . Angew. Chem. Int. Ed. , 38 : 1532 – 1568 .
  • Paulsen , H. , Kolář , Č and Stenzel , W. 1976 . Synthese α‐glycosidisch verknüpfter disaccharide des d‐galactosamins . Angew. Chem. , 88 : 478 – 479 .
  • Perry , M. B. 1979 . 2‐Acetamido‐2‐deoxy‐d‐galactose and 2‐acetamido‐2‐deoxy‐d‐talose . Methods Carb. Chem. , 7 : 32 – 35 .
  • Das , J. and Schmidt , R. R. 1998 . Convinient glycoside synthesis of amino sugars: Michael‐type addition to 2‐nitro‐d‐galactal . Eur. J. Org. Chem. , : 1609 – 1613 .
  • Lemieux , R. U. and Ratcliffe , R. M. 1979 . The azidonitration of tri‐O‐acetyl‐d‐galactal . Can. J. Chem. , 57 : 1244 – 1251 .
  • Hederos , M. and Konradsson , P. 2005 . Efficient routes to ethyl‐2‐deoxy‐2‐phthalimido‐1‐β‐d‐thio‐galactosamine derivatives via epimerisation of the corresponding glucosamine compounds . J. Carbohydr. Chem. , 24 : 297 – 320 .
  • Veselý , J. , Ledvina , M. , Jindřich , J. , Trnka , T. and Šaman , D. 2004 . Synthesis of 2‐amino‐2‐deoxy‐galactopyranosyl‐(1→4)‐2‐amino‐2‐deoxy‐b‐d‐galactopyranosides: Using various 2‐deoxy‐2‐phthalimido‐d‐galactopyranosyl donors and acceptors . Collect. Czech. Chem. Commun. , 69 : 1914 – 1938 .
  • Ágoston , K. , Kerékgyártó , J. , Hajkó , J. , Batta , G. , Lefeber , D. J. , Kamerling , J. P. and Vliegenthart , J. F.G. 2002 . Synthesis of fragments of the glycocalyx glycan of the parasite Schistosoma mansoni . Chem. Eur. J. , 8 : 151 – 161 .
  • Misra , A. K. , Fukuda , M. and Hindsgaul , O. 2001 . Efficient synthesis of lactosaminylated Core‐2 O‐glycans . Bioorg. Med. Chem. Lett. , 11 : 2667 – 2669 .
  • Ito , N. , Tokuda , Y. , Ohba , S. and Sugai , T. 2004 . An expeditious route to N‐Acetyl‐d‐galactosamine from N‐Acetyl‐d‐glucosamine based on the selective protection of hydroxy groups . Bull. Chem. Soc. Japan. , 77 : 1181 – 1186 .
  • Wrodnigg , T. M. and Eder , B. 2000 . “ The Amadori and Heyns rearrangements: landmarks in the history of carbohydrate chemistry or unrecognized synthetic opportunities? ” . In Glycoscience–Epimerization, Isomerization, Rearrangement Reactions of Carbohydrates Edited by: Stütz , A. E. 115 – 152 . Heidelberg : Springer .
  • Fischer , E. 1884 . Verbindungen des Phenylhydrazins mit den Zuckerarten . Ber. , 17 : 579 – 584 .
  • Fischer , E. 1886 . Über Isoglucosamin . Ber. , 19 : 1920 – 1924 .
  • Heyns , K. and Koch , W. 1952 . Formation of an amino sugar from d‐fructose and ammonia . Z. Naturforschung , 7b : 486 – 488 .
  • Heyns , K. , Paulsen , H. , Eichstedt , R. and Rolle , M. 1957 . The formation of 2‐aminoaldoses by rearrangement of ketosylamines . Chem. Ber. , 90 : 2039 – 2049 .
  • Weicker , H. and Gräßling , D. 1964 . Galaktosamin‐synthese aus tagatose an kieselgel‐H in wäßrigem amminokalkalischem milieu . Hoppe‐Seyler's Zeit. Physiol. Chem. , 337 : 133 – 136 .
  • Wrodnigg , T. M. and Stütz , A. R. 1999 . The Heyns rearrangement revisited: an exceptionally simple two‐step chemical synthesis of d‐lactosamine from lactulose . Angew. Chem. Int. Ed. Engl. , 38 : 827 – 828 .
  • Stütz , A. E. , Dekany , G. , Eder , B. , Illaszewicz , C. and Wrodnigg , T. M. 2003 . An exceptionally simple chemical synthesis of d‐lactosamine via the Heyns rearrangement . J. Carbohydr. Chem. , 22 ( 5 ) : 253 – 265 .
  • Levin , G. V.J. 2002 . Tagatose, the new GRAS sweetener and health product . Med. Food , 5 : 23 – 36 .
  • Beadle , J. R. , Saunders , J. P. and Wajda , T. J. Process for manifacturing tagatose . U.S. Patent 5,078796 . January 7, 1992 .
  • Ibrahem , I. and Córdova , A. 2005 . Amino acid catalyzed direct enantioselective formation of carbohydrates: one‐step de novo synthesis of ketoses . Tetrahedron Lett. , 46 : 3363 – 3367 .
  • Toth , I. , Dekany , G. and Kellman , B. Preparation of cyclic compounds as protecting and linking for organic synthesis . PTC Int. Appl. WO99 15510 .
  • Dekany , G. , Bornaghi , L. , Papageorgiou , J. and Taylor , S. 2001 . A novel amino protecting group: DTPM . Tetrahedron Lett. , 42 : 3129 – 3132 .
  • Wong , T. C. , Townsend , R. R. and Lee , Y. C. 1987 . Synthesis of d‐galactosamine derivatives and binding studies using isolated rat hepatocytes . Carbohydr. Res. , 170 : 27 – 46 .
  • Xi , Z. , Hwang , G‐S. , Goldberg , I. H. , Harris , J. L. , Pennington , W. T. , Fouad , F. S. , Qabaja , G. , Wright , J. M. and Jones , G. B. 2002 . Targeting DNA bulged microenvironments with synthetic agents: lessons from a natural product . Chem. Biol. , 9 : 925 – 931 .
  • Mikeska , T. , Nieger , M. , Maniskkamäki , H. , Daniels , J. and Kolter , T. 2003 . Crystal structures of O‐acetylated 2‐acylamino‐2‐deoxy‐d‐galactose derivatives . Carbohydr. Res. , 338 : 2119 – 2128 .

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