Synthesis of 2,3,4-Trideoxy-4,4-difluoro-d-ribo-hexopyranose
Adenosines

Jun Xu; Xingang Zhang; Xiao-Long Qiu; Feng-Ling Qing

doi:10.1055/s-0028-1083331

PAPER

Synthesis of 2,3,4-Trideoxy-4,4-difluoro-d-ribo-hexopyranose Adenosines

Jun Xu^a, Xingang Zhang^a, Xiao-Long Qiu^a, Feng-Ling Qing*^a,b
^a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
^b College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, P. R. of China
Fax: +(86)2164166128; e-Mail: flq@mail.sioc.ac.cn;

Abstract

All articles of this category

Abstract

A novel synthetic route to 2,3,4-trideoxy-4,4-difluoro-β-d-ribo-hexopyranose adenosine and 2,3,4-trideoxy-2,3-didehydro-4,4-difluoro-β-d-ribo-hexopyranose adenosine has been developed. The approach highlights the highly regio- and stereoselective palladium-catalyzed glycosylation of Boc-protected pyranose, which was prepared from the oxidation-cyclization of a difluorinated diol. The diol was provided through ozonization and Lindlar reduction of optically pure enynic alcohol.

Key words

nucleosides - fluorinated compounds - palladium-catalyzed glycosylation

Full Text

References

<A NAME="RF19008SS-1A">1a</A> Onuma S. Nawata N. Saito Y. Bull. Chem. Soc. Jpn. 1966, 39: 1091

<A NAME="RF19008SS-1B">1b</A> Nomoto S. Shimoyama A. Tetrahedron Lett. 2001, 42: 1753

<A NAME="RF19008SS-2A">2a</A> Fox JJ. Kuwada Y. Watanabe KA. Ueda T. Whipple EB. Antimicrob. Agents Chemother. 1964, 518

<A NAME="RF19008SS-2B">2b</A> Watanabe KA. Falco EA. Fox JJ. J. Am. Chem. Soc. 1972, 94: 3272

<A NAME="RF19008SS-3A">3a</A> Ennifar S. Das BC. Nash SM. Nagarajan R. J. Chem. Soc., Chem. Commun. 1977, 41

<A NAME="RF19008SS-3B">3b</A> Ikemoto N. Schreiber SL. J. Am. Chem. Soc. 1990, 112: 9657

<A NAME="RF19008SS-3C">3c</A> Ikemoto N. Schreiber SL. J. Am. Chem. Soc. 1992, 114: 2524

<A NAME="RF19008SS-4">4</A> Harada S. Mizuta E. Kishi T. J. Am. Chem. Soc. 1978, 100: 4895

<A NAME="RF19008SS-5">5</A> Recent Advances in Nucleosides: Chemistry and Chemotheropy Chu CK. Elsevier Science; Amsterdam: 2002.

<A NAME="RF19008SS-6A">6a</A> Leutzinger EE. Meguro T. Townsend LB. Shuman DA. Schweizer MP. Stewart CM. Robins RK. J. Org. Chem. 1972, 37: 3695

<A NAME="RF19008SS-6B">6b</A> Nord LD. Dalley NK. McKernan PA. Robins RK. J. Med. Chem. 1987, 30: 1044

For the synthesis of 5 and its enantiomer, see:

<A NAME="RF19008SS-7A">7a</A> Groebke K. Hunziker J. Fraser W. Peng L. Diederichsen U. Zimmermann K. Holzner A. Leumann C. Eschenmoser A. Helv. Chim. Acta 1998, 81: 375

<A NAME="RF19008SS-7B">7b</A> Boehringer M. Roth HJ. Hunziker J. Goebel M. Krishnan R. Giger A. Schweizer B. Schreiber J. Leumann C. Eschenmoser A. Helv. Chim. Acta 1992, 75: 1416

<A NAME="RF19008SS-7C">7c</A> Guppi SR. Zhou M. O’Doherty GA. Org. Lett. 2006, 8: 293

<A NAME="RF19008SS-8A">8a</A> Sabatino D. Damha MJ. J. Am. Chem. Soc. 2007, 129: 8259

<A NAME="RF19008SS-8B">8b</A> Choo J. Lee S.-N. Lee K.-H. Bull. Korean Chem. Soc. 1996, 17: 7

<A NAME="RF19008SS-8C">8c</A> Ferrier RJ. Sankey GH. J. Chem. Soc. C. 1966, 2345

<A NAME="RF19008SS-8D">8d</A> Laane J. Choo J. J. Am. Chem. Soc. 1994, 116: 3889

<A NAME="RF19008SS-9A">9a</A> Wang J. Verbeure B. Luyten I. Lescrinire E. Froeyen M. Hendrix C. Rosemeyer H. Seela F. Van Aershot A. Herdewijn P. J. Am. Chem. Soc. 2000, 122: 8595

<A NAME="RF19008SS-9B">9b</A> Schoning K.-U. Scholz P. Guntha S. Wu X. Krishnamurthy R. Eschenmoser A. Science 2000, 290: 1347

<A NAME="RF19008SS-9C">9c</A> Wilds CJ. Wawrzak Z. Krishnamurthy R. Eschenmoser A. Egli M. J. Am. Chem. Soc. 2002, 124: 13716

<A NAME="RF19008SS-10A">10a</A> Thayer AM. Chem. Eng. News 2006, (June 5): 15

<A NAME="RF19008SS-10B">10b</A> Begue JP. Bonnet-Delpon D. J. Fluorine Chem. 2006, 127: 992

<A NAME="RF19008SS-10C">10c</A> Kirk KL. J. Fluorine Chem. 2006, 127: 1013

<A NAME="RF19008SS-10D">10d</A> For recent excellent overviews, see: Ojima I. ChemBioChem 2004, 5: 628

<A NAME="RF19008SS-10E">10e</A> Chambers RD. Fluorine in Organic Chemistry Blackwell; Oxford: 2004.

<A NAME="RF19008SS-10F">10f</A> Kirsch P. Modern Fluoroorganic Chemistry Wiley-VCH; Weinheim: 2004.

<A NAME="RF19008SS-10G">10g</A> Uneyama K. Organofluorine Chemistry Blackwell; Oxford: 2006.

<A NAME="RF19008SS-10H">10h</A> Müller K. Faeh C. Diederich F. Science 2007, 317: 1881

<A NAME="RF19008SS-11">11</A> Hertel LW. Kroin JS. Misner JW. Tustin JM. J. Org. Chem. 1988, 53: 2406

<A NAME="RF19008SS-12">12</A> Pankiewicz KW. Carbohydr. Res. 2000, 327: 87

<A NAME="RF19008SS-13">13</A> Yang Y.-Y. Xu J. You ZW. Xu X.-H. Qiu X.-L. Qing F.-L. Org. Lett. 2007, 9: 5437

<A NAME="RF19008SS-14">14</A> Babu RS. O’Doherty GA. J. Am. Chem. Soc. 2003, 125: 12406

<A NAME="RF19008SS-15">15</A> You Z.-W. Jiang Z.-X. Wang B.-L. Qing F.-L. J. Org. Chem. 2006, 71: 7261

<A NAME="RF19008SS-16">16</A> De Luca L. Giacomelli G. Porcheddu A. Org. Lett. 2001, 3: 3041

Further details of the crystal structure investigation can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (CCDC deposition No. 694847).