Optimized Procedure for the Synthesis of 6‐Azido‐6‐deoxy‐galactopyranosides From 6‐O‐Tosyl‐galactopyranosides

References

• Maunier , V. , Boullanger , P. , Lafont , D. and Chevalier , Y. 1997 . Synthesis and surface‐active properties of amphiphilic 6‐aminocarbonyl derivatives of D‐glucose . Carbohydr. Res. , 299 : 49 – 57 .
   Web of Science ®Google Scholar
• Kieburg , C. , Sadalapure , K. and Lindhorst , T. K. 2000 . Glucose‐based AB2‐building blocks for the construction of branched glycopeptidomimetics . Eur. J. Org. Chem. , : 2035 – 2040 .
   Google Scholar
• Hansen , H. C. and Magnusson , G. 1999 . Synthesis of selected aminodeoxy analogues of galabiose and globotriose . Carbohydr. Res. , 322 : 166 – 180 .
   PubMedGoogle Scholar
• Szarek , W. A. and Jones , J. K. N. 1965 . Carbohydrates containing nitrogen in a five‐membered ring and an attempted synthesis of a carbohydrate with nitrogen in a seven‐membered ring . Can. J. Chem. , 43 : 2345 – 2356 .
   Google Scholar
• Bullock , C. , Hough , L. and Richardson , A. C. 1990 . A novel route to 1,4‐anhydro derivatives of β‐D‐galactopyranose . Carbohydr. Res. , 197 : 131 – 138 .
   Google Scholar
• Yoshimura , J. , Asano , K. , Umemura , K. , Horito , S. and Hashimoto , H. 1983 . Synthesis of methyl 2,3‐O‐D‐glycopyranosylidene‐α‐D‐mannopyranosides having various substituents . Carbohydr. Res. , 121 : 187 – 204 .
   Google Scholar
• Hui , Y. and Chang , C. T. 2002 . Convenient divergent synthesis of a library of trehalosamine analogues . Org. Lett. , 4 ( 13 ) : 2245 – 2248 .
   PubMedGoogle Scholar
• Blanco , J. L. J. , Fernandez , J. M. G. , Gadelle , A. and Defaye , J. 1997 . A mild one‐step selective conversion of primary hydroxyl groups into azides in mono‐ and oligo‐saccharides . Carbohydr. Res. , 303 : 367 – 372 .
   Google Scholar
• Moris‐Varas , F. , Qian , X. H. and Wong , C. H. 1996 . Enzymatic/chemical synthesis and biological evaluation of seven‐membered iminocyclitols . J. Am. Chem. Soc. , 118 : 7647 – 7652 .
   Google Scholar
• Lafont , D. and Boullanger , P. 1999 . Preparation of primary and secondary azidosugars from diols using the dioxaphosphorane methodology . J. Carbohydr. Chem. , 18 : 675 – 688 .
   Web of Science ®Google Scholar
• Kobayashi , Y. and Shiozaki , M. 1995 . Syntheses of trehazolin derivatives and evaluation as glycosides inhibitors . J. Org. Chem. , 60 : 2570 – 2580 .
   Google Scholar
• Christian , S. , Ralf , M. and Helmut , R. 2002 . Non‐anomeric sugar isoureas . J. Carbohydr. Chem. , 21 : 293 – 304 .
   Google Scholar
• Wu , M. , Anderson , L. , Slife , C. W. and Jenson , L. J. 1974 . Effect of solvent, temperature, and nature of sulfonate group on the azide displacement reaction of sugar sulfonates . J. Org. Chem. , 39 ( 20 ) : 3014 – 3019 .
   Google Scholar
• Sugihara , J. M. , Teerlink , W. J. , MacLeod , R. , Dorrence , S. M. and Springer , C. 1963 . Direct syntheses of some cyano and nitro derivatives of carbohydrates by nucleophilic displacement . J. Org. Chem. , 28 : 2079 – 2082 .
   Google Scholar
• Carmen , L. , Romero , Z. and Oscar , V. 2001 . Synthesis of 6‐amino‐6‐deoxy‐2,3,4,5‐tetra‐O‐methyl‐D‐galactonic acide, a key precursor of a steroregular polyamide . J. Carbohydr. Chem. , 20 : 689 – 701 .
   Google Scholar
• Patel , A. and Lindhorst , T. K. 2002 . Synthesis of “mixed type” oligosaccharide mimetics based on a carbohydrate scaffold . Eur. J. Org. Chem. , : 79 – 86 .
   Google Scholar
• See Roslund , M. U. , Klika , K. D. , Lehtilä , R. L. , Tähtinen , P. , Sillanpää , R. and Leino , R. 2004 . Conformation of the galactose ring adopted in solution and in crystalline form as determined by experimental and DFT 1H NMR and single‐crystal X‐ray analysis . J. Org. Chem. , 69 : 18 – 25 . 1,2,3, 4‐di‐O‐isopropylidene‐α‐D‐galactopyranoside adopted a skew‐boat conformation.
   PubMedGoogle Scholar
• Joosten , J. A. F. , Evers , B. , van Summeren , R. P. , Kamerling , J. P. and Vliegenthart , J. F. G. 2003 . Synthesis of β‐D‐Galp‐(1→4)‐β‐D‐GlcpNAc‐(1→2)‐α‐D‐Manp‐(1→O)‐(CH2)7CH3 mimics to explore the substrate specificity of sialyltransferases and trans‐sialidases . Eur. J. Org. Chem. , : 3569 – 3586 .
   Google Scholar