Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(5): 0598-0600
DOI: 10.1055/s-2002-23551
DOI: 10.1055/s-2002-23551
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement [1]
Further Information
Received
10 November 2001
Publication Date:
02 April 2002 (online)
Publication History
Publication Date:
02 April 2002 (online)

Abstract
The reaction of tri-O-acetyl-d-glucal and tri-O-benzyl-d-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
Key words
Ferrier rearrangement - carbohydrates - bismuth trichloride - unsaturated glycopyranosides
IICT Communication No. 01/09/07.
-
2a
Fraser-Reid B. Acc. Chem. Res. 1985, 18: 347 -
2b
Ferrier RJ. Adv. Carbohydr. Chem. Biochem. 1969, 24: 199 -
3a
Winterfeld GA. Ph.D. Dissertation University of Konstanz; Germany: 2000. -
3b
Durgan BJ.Jackson RFW. Synlett 1996, 859 - 4
Schmidt RR.Angerbauer R. Angew.Chem., Int. Ed. Engl. 1977, 16: 783 ; Angew. Chem. 1977, 89, 822 -
5a
Schmidt RR.Angebauer R. Carbohydr. Res. 1979, 72: 272 -
5b
Bracherro MP.Cabrera EF.Gomez GM.Peredes LMR. Carbohydr. Res. 1998, 181: 308 - 6
Williams NR.Wander JD. The Carbohydrates: Chemistry and Biochemistry Academic Press; New York: 1980. p.761 - 7
Ferrier RJ.Prasad NJ. J. Chem. Soc. C 1969, 570 -
8a
Descotes G.Martin JC. Carbohydr. Res. 1977, 56: 168 -
8b
Klaffke W.Pudlo P.Springer D.Thiem J. Liebigs Ann. Chem. 1991, 509 -
9a
Grynkiewicz G.Priebe W.Zamojski A. Carbohydr.Res. 1979, 68: 33 -
9b
Bhate P.Horton D.Priebe W. Carbohydr. Res. 1985, 144: 331 - 10
Toshima K.Ishizuka T.Malsuo G.Nakata M. Synlett 1995, 306 - 11
Toshima K.Ishizuka T.Matsuo G.Nakata M.Konoshita M. J. Chem. Soc.,Chem.Commun. 1993, 704 - 12
Fraser-Reid B.Madsen R. J. Org. Chem. 1995, 60: 3851 - 13
Babu BS.Balasubramanian KK. Tetrahedron Lett. 2000, 41: 1271 - 14
Yadav JS.Reddy BVS.Murthy CVSR.Kumar GM. Synlett 2000, 1450 - 15
Takhi M.Abdel-Rahman Adel A.-H.Schmidt RR. Synlett 2001, 427 - 16
Dearg SB.Steven VL.Sadie V.Mervyn T. Tetrahedron 1991, 47: 1329 - 17
Frappa I.Sinou D. Synth. Commun. 1995, 25: 2941 - 18
Lesueur C.Nouguier R.Bertrand MP.Hoffmann P.De Mesmeker E. Terahedron 1994, 50: 5369 - 19
Moufid N.Chapleur Y.Mayon P. J. Chem. Soc., Perkin Trans.1 1992, 999 - 20
Valverde S.Garcia-Ochoa S. J. Carbohydr. Chem. 1989, 8: 553
Reference
IICT Communication No. 01/09/07.