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Synthesis 2006(13): 2117-2120
DOI: 10.1055/s-2006-942407
DOI: 10.1055/s-2006-942407
PAPER
© Georg Thieme Verlag Stuttgart · New York
Novel Approach towards C-C-Linked Carbohydrate Dimers via Claisen Rearrangement of a Disaccharide Allyl Ketene Acetal
Further Information
Received
11 April 2006
Publication Date:
08 June 2006 (online)
Publication History
Publication Date:
08 June 2006 (online)
Abstract
A disaccharide derivative was synthesised by coupling tri-O-benzyl-d-glucal with an allylic sugar alcohol in a glycosyloxyselenation reaction. Subsequent oxidation followed by syn-elimination of the selenoxide and in situ rearrangement of the intermediate allyl ketene acetal gave novel C-C-linked saccharide dimers.
Key Words
mimetics - carbohydrates - selenium - allyl ketene acetals - rearrangements
- 1
Chapleur Y. Carbohydrate Mimics: Concepts and Methods Wiley-VCH; Weinheim: 1998. -
2a
Duda CA.Stevens ES. J. Am. Chem. Soc. 1993, 115: 8487 -
2b
Ferritto R.Vogel P. Tetrahedron: Asymmetry 1994, 5: 2077 -
2c
O’Leary DJ.Kishi Y. Tetrahedron Lett. 1994, 35: 5591 - 3
Paton RM.Penman KJ. Tetrahedron Lett. 1994, 35: 3163 - 4
Schmidt RR.Beyerbach A. Liebigs Ann. Chem. 1992, 983 - 5
Ishida N.Kumagai K.Niida T.Tsuruoka T.Yumoto H. J. Antibiot. 1967, 20: 66 - 6
Taylor DL.Fellows LE.Farrar GH.Nash RJ.Taylor-Robinson D.Mobberley MA.Ryder TA.Jeffries DJ.Tyms AS. Antiviral Res. 1988, 10: 11 - 7
Nishimura Y.Satoh T.Adachi H.Kondo S.Takeuchi T.Azetaka M.Fukuyasu H.Iizuka Y. J. Am. Chem. Soc. 1996, 118: 3051 - 8
Werschkun B.Thiem J. Tetrahedron: Asymmetry 2005, 16: 569 - 9
Franz AH.Gross PH. Carbohydr. Lett. 1997, 2: 371 - 10
Ferrier RJ.Prasad N. J. Chem. Soc. 1969, 570 - 11
Zemplén G.Gerecs A.Hadácsy I. Ber. Dtsch. Chem. Ges. 1936, 69: 1827 -
12a
Jaurand G.Beau J.-M.Sinaӱ P. J. Chem. Soc., Chem Commun. 1982, 572 -
12b
Jaurand G.Beau J.-M.Sinaӱ P. J. Chem. Soc., Chem Commun. 1982, 701 - 13
Reich HJ.Wollowitz S.Trend JE.Chow F.Wendelborn DF. J. Org. Chem. 1978, 43: 1697 - 14
Petrzilka M. Helv. Chim. Acta 1978, 61: 2286 - 15
Eaton PE.Andrews GD.Krebs E.-P.Kunai A. J. Org. Chem. 1979, 44: 2824 - 16
Waaszek Z.Horton D.Ekiel I. Carbohydr. Res. 1982, 106: 193 - 17
Hackert ML.Jacobson RA. Acta Cryst. 1971, B27: 203 - 18
Bierenstiel M.Schlaf M. Eur. J. Org. Chem. 2004, 1474 - 19
Nelson CR. Carbohydr. Res. 1982, 106: 155 - 20
Mieczkowski J.Konowal A.Zamojski A. Pol. J. Chem. 1983, 57: 75 ; Chem. Abstr. 1984, 101, 7560