C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone.
作者： Yusuke Masuda , Hiromu Tsuda , Masahiro Murakami
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摘要: Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light the presence of water-soluble benzophenone. Whereas its anomeric carbon (C1) is oxidized to carboxy group, hydroxy group on C2 replaced by hydrogen. The generated 2-deoxy lactones are readily reduced corresponding aldoses, which often contained bioactive compounds.
sci-hub.se 参考文章(55)
DH Dolphin, AW Johnson, R Rodrigo, N Shaw, The vitamin B12 coenzyme Pure and Applied Chemistry. ,vol. 7, pp. 539- 550 ,(1963) , 10.1021/AR50099A006
Arne N. Wick, Douglas R. Drury, Henry I. Nakada, Jack B. Wolfe, Barbara Britton, Ruth Grabowski, LOCALIZATION OF THE PRIMARY METABOLIC BLOCK PRODUCED BY 2-DEOXYGLUCOSE Journal of Biological Chemistry. ,vol. 224, pp. 963- 969 ,(1957) , 10.1016/S0021-9258(18)64988-9
Frank Urban, Philip A. Shaffer, THE ACIDIC PROPERTY OF SUGARS Journal of Biological Chemistry. ,vol. 94, pp. 697- 715 ,(1932) , 10.1016/S0021-9258(18)76394-1
Joseph A. Cradlebaugh, Li Zhang, G. Robert Shelton, Grzegorz Litwinienko, Bruce E. Smart, Keith U. Ingold, William R. Dolbier, Jr., Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process Organic and Biomolecular Chemistry. ,vol. 2, pp. 2083- 2086 ,(2004) , 10.1039/B405074F
Perry A. Frey, Importance of organic radicals in enzymic cleavage of unactivated carbon-hydrogen bonds Chemical Reviews. ,vol. 90, pp. 1343- 1357 ,(1990) , 10.1021/CR00105A014
Elson Santiago de Alvarenga, John Mann, Photocatalysed addition of pyrrolidines to butenolides: a concise synthesis of the pyrrolizidine alkaloid ring system Journal of the Chemical Society, Perkin Transactions 1. pp. 2141- 2142 ,(1993) , 10.1039/P19930002141
Derek Horton, Waldemar Priebe, Marcos L. Sznaidman, Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane Journal of Organic Chemistry. ,vol. 58, pp. 1821- 1826 ,(1993) , 10.1021/JO00059A037
Matthew P. McLaughlin, Laura L. Adduci, Jennifer J. Becker, Michel R. Gagné, Iridium-catalyzed hydrosilylative reduction of glucose to hexane(s). Journal of the American Chemical Society. ,vol. 135, pp. 1225- 1227 ,(2013) , 10.1021/JA3110494
Dianjie Hou, Todd L. Lowary, Recent advances in the synthesis of 2-deoxy-glycosides. Carbohydrate Research. ,vol. 344, pp. 1911- 1940 ,(2009) , 10.1016/J.CARRES.2009.07.013
Samuel Bertrand, Norbert Hoffmann, Stéphane Humbel, Jean Pierre Pete, Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET). Journal of Organic Chemistry. ,vol. 65, pp. 8690- 8703 ,(2000) , 10.1021/JO001166L