An Efficient Synthesis of β-C-Glycosides Based on the Conformational Restriction Strategy: Lewis Acid Promoted Silane Reduction of the Anomeric Position with Complete Stereoselectivity

作者: Masaru Terauchi , Hiroshi Abe , Akira Matsuda , Satoshi Shuto

DOI: 10.1021/OL048525+

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摘要: The reduction of glyconolactols having an anomeric carbon substituent by Et3SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding β-C-glycosides when substrates were conformationally restricted in 4C1-chair form a 3,4-O-cyclic diketal or 4,6-O-benzylidene protecting group. Thus, efficient construction was achieved on basis conformation restriction strategy.

参考文章(24)
Thomas G. Minehan, Yoshito Kishi, β-selective C-glycosidations: lewis-acid mediated reactions of carbohydrates with silyl ketene acetals Tetrahedron Letters. ,vol. 38, pp. 6815- 6818 ,(1997) , 10.1016/S0040-4039(97)01602-X
David Crich, Weiling Cai, Zongmin Dai, Highly Diastereoselective α-Mannopyranosylation in the Absence of Participating Protecting Groups Journal of Organic Chemistry. ,vol. 65, pp. 1291- 1297 ,(2000) , 10.1021/JO9910482
Yuguo Du, Robert J. Linhardt, Iontcho R. Vlahov, Recent advances in stereoselective c-glycoside synthesis Tetrahedron. ,vol. 54, pp. 9913- 9959 ,(1998) , 10.1016/S0040-4020(98)00405-0
Martin de Kort, Anouk D. Regenbogen, A. Rob P. M. Valentijn, R. A. John Challiss, Yoriko Iwata, Shuichi Miyamoto, Gijs A. van der Marel, Jacques H. van Boom, Spirophostins: Conformationally Restricted Analogues of Adenophostin A Chemistry - A European Journal. ,vol. 6, pp. 2696- 2704 ,(2000) , 10.1002/1521-3765(20000804)6:15<2696::AID-CHEM2696>3.0.CO;2-Y
Michael D. Lewis, Jin Kun Cha, Yoshito Kishi, Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides Journal of the American Chemical Society. ,vol. 104, pp. 4976- 4978 ,(1982) , 10.1021/JA00382A053
Andrzej Stanislaw Cieplak, Stereochemistry of Nucleophilic Addition to Cyclohexanone. The Importance of Two-Electron Stabilizing Interactions Journal of the American Chemical Society. ,vol. 103, pp. 4540- 4552 ,(1981) , 10.1021/JA00405A041
Eusebio Juaristi, Gabriel Cuevas, Recent studies of the anomeric effect Tetrahedron. ,vol. 48, pp. 5019- 5087 ,(1992) , 10.1016/S0040-4020(01)90118-8