Download PDF
Synthesis 2010(10): 1617-1620  
DOI: 10.1055/s-0029-1218722
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Stereoselective Synthesis of 2,3-Unsaturated Thioglycopyranosides Employing Molecular Iodine

Basi V. Subba Reddy*a, Ch. Divyavania,b, Jhillu S. Yadava
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in ;
b IICT - An Associate Institution of the University of Hyderabad, Hyderabad 500007, India
Further Information

Publication History

Received 29 January 2010
Publication Date:
06 April 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

Molecular iodine has been utilized for the first time for the thioglycosidation of d-glycals with various thiols to afford the corresponding 2,3-unsaturated thioglycosides in high yields. In the case of tri-O-acetyl-d-glucal, the α-anomer was obtained exclusively. The use of readily available iodine makes this method quite simple, more convenient, and practical.

Key words

glycals - iodine - thioglycosides - thia-Ferrier rearrangement

    References

  • 1a Sinay P. Pure Appl. Chem.  1991,  63:  519 
    Google Scholar
  • 1b Halcomb RL. Wittman MD. Olson SH. Danishefsky SJ. Golik J. Wong H. Vyas D. J. Am. Chem. Soc.  1991,  113:  5080 
    Google Scholar
  • 2 Fukase K. Nakai Y. Kanoh T. Kusumoto S. Synlett  1998,  84 
    Article in Thieme ConnectGoogle Scholar
  • 3a Ferrier RJ. Adv. Carbohydr. Chem. Biochem.  1969,  24:  199 
    Google Scholar
  • 3b Ferrier RJ. Prasad N. J. Chem. Soc. C.  1969,  570 
    Google Scholar
  • 3c Fraser-Reid B. Acc. Chem. Res.  1985,  18:  347 
    Google Scholar
  • 4 Priebe W. Zamojski A. Tetrahedron  1980,  36:  287 
    CrossrefGoogle Scholar
  • 5a Dunkerton LV. Adair NK. Euske JM. Brady KT. Robinson PD. J. Org. Chem.  1988,  53:  845 
    Google Scholar
  • 5b Blattner R. Ferrier RJ. Furneaux RH. Tetrahedron: Asymmetry  2000,  11:  379 
    Google Scholar
  • 6 Babu BS. Balasubramanian KK. Tetrahedron Lett.  1999,  40:  5777 
    CrossrefGoogle Scholar
  • 7 Yadav JS. Reddy BVS. Geetha V. Synth. Commun.  2003,  33:  717 
    CrossrefGoogle Scholar
  • 8a Yadav JS. Reddy BVS. Premalatha K. Swamy T. Tetrahedron Lett.  2005,  46:  2687 
    Google Scholar
  • 8b Huang G. Isobe M. Tetrahedron  2001,  57:  10241 
    Google Scholar
  • 8c Tsukiyama T. Peters SC. Isobe M. Synlett  1993,  413 
    Google Scholar
  • 8d Hosokawa S. Kirschbaum B. Isobe M. Tetrahedron Lett.  1998,  39:  1917 
    Google Scholar
  • 8e Tsukiyama T. Isobe M. Tetrahedron Lett.  1992,  33:  7911 
    Google Scholar
  • 9a Togo H. Iida S. Synlett  2006,  2159 
    Google Scholar
  • 9b Banik BK. Fernandez M. Alvarez C. Tetrahedron Lett.  2005,  46:  2479 
    Google Scholar
  • 9c Kartha KPR. Ballell L. Bilke J. McNeil M. Field RA. J. Chem. Soc., Perkin Trans. 1  2001,  770 
    Google Scholar
  • 9d Koreeda M. Houston TA. Shull BK. Klemke E. Tuinman RJ. Synlett  1995,  90 
    Google Scholar
  • 9e Vaino RK. Szarek WA. Synlett  1995,  1157 
    Google Scholar
  • 9f Lipshutz BH. Keith J. Tetrahedron Lett.  1998,  39:  2495 
    Google Scholar
  • 9g Ko S. Sastry MNV. Lin C. Yao CF. Tetrahedron Lett.  2005,  46:  5771 
    Google Scholar
  • 10a Yadav JS. Reddy BVS. Hashim SR. J. Chem. Soc., Perkin Trans. 1  2000,  3082 
    Google Scholar
  • 10b Yadav JS. Reddy BVS. Sabitha G. Reddy GSKK. Synthesis  2000,  1532 
    Google Scholar
  • 10c Yadav JS. Reddy BVS. Rao CV. Rao KV. J. Chem. Soc., Perkin Trans. 1  2002,  1401 
    Google Scholar
  • 10d Yadav JS. Reddy BVS. Rao CV. Chand PK. Prasad AR. Synlett  2001,  1638 
    Google Scholar
  • 10e Yadav JS. Reddy BVS. Narayana Kumar GGKS. Swamy T. Tetrahedron Lett.  2007,  48:  2205 
    Google Scholar
  • 11 Kirby AJ. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen   Spinger-Verlag; New York: 1983. 
    Google Scholar