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Synthesis 2006(9): 1499-1503
DOI: 10.1055/s-2006-926422
DOI: 10.1055/s-2006-926422
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of C-Glucoside endo-Glycals from C-Glucosyl Vinyl Sulfones
Weitere Informationen
Received
12 December 2005
Publikationsdatum:
07. April 2006 (online)
Publikationsverlauf
Publikationsdatum:
07. April 2006 (online)
![](https://www.thieme-connect.de/media/synthesis/200609/lookinside/thumbnails/10.1055-s-2006-926422-1.jpg)
Abstract
The synthesis and the reactivity of C-glucosyl vinyl sulfones in two steps from benzylated gluconolactone and benzothiazolylsulfones derivatives is reported.
Key words
vinyl sulfones - C-glycosides - exo-glycals - ipso substitution
-
1a
Wiley PF.Mac Kellar EL.Carton EL.Kelly RB. Tetrahedron Lett. 1968, 8: 663 -
1b
Horton D.Philips KD. Carbohydr. Res. 1973, 30: 367 -
1c
Kaye A.Neidle S.Reese CB. Tetrahedron Lett. 1988, 29: 1841 -
2a
Schafer A.Thiem J. J. Org. Chem. 2000, 65: 24 -
2b
Nicotra F. Top. Curr. Chem. 1997, 187: 55 - 3
Taillefumier C.Chapleur Y. Chem. Rev. 2004, 104: 263 -
4a
Brockhaus M.Lehmann J. Carbohydr. Res. 1977, 53: 21 -
4b
Lehmann J.Schwesinger B. Carbohydr. Res. 1982, 107: 43 -
5a
Gervay J.Flaherty TM.Holmes D. Tetrahedron 1997, 53: 16355 -
5b
Rubinstein G.Mallet JM.Sinaӱ P. Tetrahedron Lett. 1998, 39: 3697 -
5c
Wilcox CS.Long GW.Suh H. Tetrahedron Lett. 1984, 25: 395 -
6a
Aucagne V.Gueyrard D.Tatibouet A.Quinsac A.Rollin P. Tetrahedron 2000, 56: 2647 -
6b
Goekjian PG.Wei A.Kishi Y. Conformational Analysis of C-Glycosides and Related Compounds: Programming Conformational Profiles of C-and O-Glycosides, In Carbohydrate-based Drug DiscoveryWong C.-H. Wiley-VCH; Weinheim: 2003. Chap. 11: p.305-340 - 7
Gueyrard D.Haddoub R.Salem A.Said Bacar N.Goekjian PG. Synlett 2005, 520 - 8
Jacobs HK.Gopalan AS. J. Org. Chem. 1994, 59: 2014 - 9
Lacrampe F.Leost F.Doutheau A. Tetrahedron Lett. 2000, 41: 4773 - 10
Yang WB.Yang YY.Gu YF.Wang SH.Chang CC.Lin CH. J. Org. Chem. 2002, 67: 3773 - 12
Oae S.Furukawa N. Adv. Heterocycl. Chem. 1990, 48: 1 -
13a
Lorin C.Rollin P. Synthesis 1998, 1506 -
13b
Gueyrard D.Lorin C.Moravcova J.Rollin P. J. Carbohydr. Chem. 1999, 18: 317 -
14a
Richert C.Roughton AL.Benner SA. J. Am. Chem. Soc. 1996, 118: 4518 -
14b
Carchon G.Chretien F.Chapleur Y. Tetrahedron Lett. 2003, 44: 5715
References
The configuration of the double bond has been determined by NOE experiments. A correlation has been observed between the vinylic proton and H-2.