Synthesis of “Reversed” Pyrazole‐C‐nucleoside Precursors from Push‐pull Activated Monosaccharide Derivatives

References

• Zhang , H. Y. , Yu , H. W. , Ma , L. T. , Min , J. M. and Zhang , L. H. 1998 . Synthesis of 2‐C‐(4‐aminocarbonyl‐2‐thiazoyl)‐1,4‐anhydro‐L‐xylitols and their fluoro derivatives . Tetrahedron Asymmetry , 9 : 141 – 149 .
   Google Scholar
• Yu , H. W. , Zhang , H. Y. , Yang , Z. J. , Min , J. M. , Ma , L. T. and Zhang , L. H. 1998 . Studies on the synthesis and biological activities of isonucleosides . Pure Appl. Chem. , 70 : 435 – 438 .
   Web of Science ®Google Scholar
• Yang , Z. J. , Yu , H. W. , Min , J. M. , Ma , L. T. and Zhang , L. H. 1997 . Stereoselective synthesis of 4‐deoxy‐4‐nucleobase‐2,5‐anhydro‐L‐mannitol derivatives . Tetrahedron Asymmetry , 8 : 2739 – 2747 .
   Google Scholar
• Lehmann , J. , Steck , J. and Weiser , W. 1988 . Malto‐oligosaccharide homologues of 3,7‐anhydro‐2‐azi‐1,2‐dideoxy‐d‐glycero‐d‐gulo‐octitol, improved photoaffinity reagents for labeling the malto‐oligosaccharide binding protein of Escherichia coli . Carbohydr. Res. , 184 : 113 – 120 .
   PubMed Web of Science ®Google Scholar
• Casiraghi , G. , Cornia , M. , Rassu , G. , Sante , C. D. and Spanu , P. 1992 . Synthesis and transformation of pyrrole C‐glycoconjugates . Tetrahedron , 48 : 5619 – 5628 .
   Web of Science ®Google Scholar
• Michalik , D. and Peseke , K. 2000 . Synthesis of pyrazole iso‐C‐nucleosides . J. Carbohydr. Chem. , 19 : 1049 – 1057 .
   Web of Science ®Google Scholar
• Taboada , L. H. , Feist , H. , Quincoces , J. , Michalik , M. and Peseke , K. 2004 . Synthesis of C‐nucleoside analogues starting from 1‐(Methyl‐3‐O‐benzylidene‐2‐deoxy‐α‐d‐altropyranosid‐2‐yl)‐4‐phenyl‐but‐3‐yn‐2‐one . J. Carbohydr. Chem. , 23 : 329 – 339 .
   Google Scholar
• Kartha , K. P.R. 1986 . Iodine, a novel catalyst in carbohydrate reactions. Part I. O‐isopropylidenation of carbohydrates . Tetrahedron Letters , 27 : 3415 – 3416 .
   Web of Science ®Google Scholar
• Bessodes , M. , Shamsazar , J. and Antonakis , K. 1988 . Crown ether catalyzed O‐alkylation of carbohydrates and nucleosides . Synthesis , : 560 – 562 .
   Google Scholar
• Whistler , R. L. and Lake , W. C. 1963 . Methods Carbohydrate Chemistry Vol. II , 286 – 290 . New York, London : Academic Press Inc. .
   Google Scholar
• Mereyala , H. B. , Goud , P. M. , Gadikota , R. R. and Reddy , K. R. 2000 . Transformation of terminal diols of cyclic and acyclic saccharides to epoxides and alkenes by reaction with triphenylphosphine, imidazole and iodine . J. Carbohydr. Chem. , 19 : 1211 – 1222 .
   Web of Science ®Google Scholar
• Weidmann , H. and Schwarz , H. 1972 . Eliminierungen an Penturon‐ und Hepturonsäurederivaten . Monatschefte Chemie , 103 : 218 – 228 .
   Google Scholar
• Herscovici , J. and Antonakis , K. 1980 . Molecular sieve‐assisted oxidations: New methods for carbohydrate derivative oxidation . J. Chem. Soc. Chem. Comm. , : 561 – 562 .
   Google Scholar
• Kuhla , B. , Peseke , K. , Thiele , G. and Michalik , M. 2000 . An approach to C‐branched and heterocyclic anellated pyranosides by reaction of α‐d‐erythro‐hexopyranosid‐2‐ulose with orthoformic acid derivatives . J. Prakt. Chem. , 342 : 240 – 244 .
   Google Scholar
• Gomez , M. , Quincoces , J. , Kuhla , B. , Peseke , K. and Reinke , H. 1999 . Synthesis of push‐pull derivatives of Levoglucosenone as precursors of annellated pyranosides . J. Carbohydr. Chem. , 18 : 57 – 68 .
   Web of Science ®Google Scholar
• Peseke , K. , Feist , H. , Hanefeld , W. , Kopf , J. and Schulz , H. 1995 . Branched‐chain sugars as push‐pull butadienes . J. Carbohydr. Chem. , 14 : 317 – 325 .
   Web of Science ®Google Scholar
• Dieter , R. K. 1986 . α‐Oxo ketene dithioacetals and related compounds: Versatile three‐carbon synthon . Tetrahedron , 42 : 3029 – 3095 .
   Web of Science ®Google Scholar
• Peseke , K. , Feist , H. and Cuny , E. 1992 . Synthesis of branched chain sugars with push‐pull functionality . Carbohydr. Res. , 230 : 319 – 324 .
   PubMed Web of Science ®Google Scholar
• Meisel , R. , Peseke , K. and Reinke , H. 1998 . Synthesis and reactions of derivatives of 2‐deoxyoct‐3‐ulosonic acids . J. Carbohydr. Chem. , 17 : 1083 – 1094 .
   Web of Science ®Google Scholar