Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

References

• Jain , R. and Danziger , L. H. 2004 . The macrolide antibiotics: a pharmacokinetic and pharmacodynamic overview . Curr. Pharm. Des. , 10 : 3045 – 3053 .
   PubMed Web of Science ®Google Scholar
• Parang , K. , Wiebe , L. I. and Knaus , E. E. 2000 . Novel approaches for designing 5′‐O‐ester prodrugs of 3′‐azido‐2′,3′‐dideoxythymidine (AZT) . Curr. Med. Chem. , 7 : 995 – 1039 .
   PubMed Web of Science ®Google Scholar
• Tsubomura , T. , Ogawa , M. , Yano , S. , Kobayashi , K. , Sakurai , T. and Yoshikawa , S. 1990 . Highly active antitumor platinum(II) complexes of amino sugars . Inorg. Chem. , 29 : 2622 – 2626 .
   Web of Science ®Google Scholar
• Storr , T. , Fisher , C. L. , Mikata , Y. , Yano , S. , Adam , M. J. and Orvig , C. 2005 . A glucosamine‐dipicolylamine conjugate of 99mTc(I) and 186Re(I) for use in imaging and therapy. Dalton Trans . 4 : 654 – 655 .
   Google Scholar
• Yano , S. , Inoue , S. , Nouchi , R. , Mogami , K. , Shinohara , Y. , Yasuda , Y. , Kato , M. , Tanase , T. , Kakuchi , T. , Mikata , Y. , Suzuki , T. and Yamamoto , Y. 1998 . Antifungal nickel(II) complexes derived from amino sugars against pathogenic yeast, Candida albicans . J. Inorg. Biochem. , 69 : 15 – 23 .
   PubMedGoogle Scholar
• Wegner , R. , Gottschaldt , M. , Görls , H. , Jäger , E.‐G. and Klemm , D. 2000 . New building blocks for the design of oligonuclear copper complexes based on amino carbohydrates . Angew. Chem. Int. Ed , 39 : 595 – 599 .
   PubMed Web of Science ®Google Scholar
• Gottschaldt , M. , Wegner , R. , Görls , H. , Klüfers , P. , Jäger , E.‐G. and Klemm , D. 2004 . Binuclear opper(II) complexes of 5‐N‐(β‐ketoen)amino‐5‐deoxy‐1,2‐O‐isopropylidene‐α‐d‐glucofuranose: synthesis structure, catecholoxidase activity . Carbohydr. Res. , 339 : 1941 – 1952 .
   PubMedGoogle Scholar
• Wegner , R. , Gottschaldt , M. , Poppitz , W. , Jäger , E.‐G. and Klemm , D. 2003 . Catechol oxidase model compounds based on aminocarbohydrates: new structure types and investigations on the catalytic reaction . J. Mol. Catal. A Chem. , 201 : 93 – 118 .
   Google Scholar
• Yan , S. and Klemm , D. 2002 . Mild and efficient synthesis of 5,6‐diamino‐5,6‐dideoxy‐1,2‐O‐isopropylidene‐3‐O‐methyl‐β‐l‐idofuranose: precursor of the first carbohydrate‐derived chiral Mn(III)‐salen complex. Tetrahedron . 58 : 10065 – 10071 .
   Google Scholar
• Wentworth , P. Jr. , Wiemann , T. and Janda , K. D. 1996 . A new class of pentacoordinate ribonuclease inhibitors: Synthesis, characterization, and inhibition studies of ribonucleoside and anhydropentafuranose oxorhenium(V) complexes . J. Am. Chem. Soc. , 118 : 12521 – 12527 .
   Web of Science ®Google Scholar
• Gottschaldt , M. , Koth , D. and Görls , H. 2005 . Synthesis and crystal structure of a salene type copper(II) complex derived from 3,5′‐O‐dimethyl‐2′,3′‐diamino‐2′,3′‐dideoxy‐β‐d‐xylo‐uridine . Org. Biomol. Chem. , 3 : 1170 – 1171 .
   PubMedGoogle Scholar
• Lin , T. S. , Zhou , R. X. , Scanlon , K. J. , Brubaker , W. Jr. , Lee , J. J.S. , Woods , K. , Humphreys , C. and Prusoff , W. H. 1986 . Synthesis and biological activity of several aminonucleoside‐platinum(II) complexes . J. Med. Chem. , 29 : 681 – 686 .
   PubMedGoogle Scholar
• Vorbrüggen , H. and Ruh‐Pohlenz , C. 2001 . Handbook of Nucleoside Synthesis New York : John Wiley & Sons .
   Google Scholar
• Brimacombe , J. S. and Mofti , A. M. 1971 . Nucleophilic displacement reactions in carbohydrates part xvi. Syntheses of 3,5‐diacetamido‐3,5‐dideoxy‐d‐ribose and 3,5‐diacetamido‐3,5‐dideoxy‐d‐xylose derivatives . Carbohydr. Res. , 16 : 167 – 176 .
   Google Scholar
• Ozols , A. M. , Azhayev , A. V. , Krayevsky , A. A. , Ushakow , A. S. , Gunchev , N. V. and Gottikh , B. P. 1980 . Aminonucleosides and their derivatives; VII. Synthesis of 3′,5′‐dideoxy‐3′,5′‐diaminonucleosides. Synthesis . 7 : 559 – 561 .
   Google Scholar
• Moravcova , J. , Spilova , L. , Capkova , J. , Chery , F. and Rollin , P. 2000 . Mitsunobu transformations of 1,2‐O‐isopropylidene‐α‐d‐pentofuranoses mediated by zinc salts . Collect. Czech. Chem. Commun. , 65 : 1745 – 1753 .
   Web of Science ®Google Scholar
• Graef , S. and Braun , M. 1993 . De‐novo synthesis of enantiomerically pure deoxy‐ and aminodeoxyfuranosides . Liebigs Ann. Chem. , 10 : 1091 – 1098 .
   Google Scholar
• Unger , F. M. , Christian , R. and Waldstätten , P. 1979 . Regiospecific synthesis of azidodeoxy and diazidodideoxy derivatives of methyl‐α‐d‐arabinofuranoside . Carbohydr. Res. , 69 : 71 – 77 .
   Web of Science ®Google Scholar