Recherches dans la série des cyclitols XLII. Synthèses de cyclitols tout‐cis dérivés du cyclopentane; préparation des cyclopentane‐tétrol et ‐ pentol tout‐cis

作者: F. G. Cocu , Th. Posternak

DOI: 10.1002/HLCA.19710540619

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摘要: All-cis cyclitols derived from cyclopentane have been prepared in two ways: (i) by LiAlH4 reduction of all-cis epoxypolyos; (ii) dimethyl sulfoxide treatment, the presence sodium hydrogencarbonate, brominated derivatives containing a neighbouring benzoyloxy group; under these conditions, halogen is replaced cis-oriented hydroxyl group. Thus cyclopentane-tetrol and -pentol prepared; their configuration has confirmed NMR. spectroscopy.

参考文章(24)
B. Tolbert, R. Steyn, J.A. Franks, H.Z. Sable, Studies on cyclic polyols Carbohydrate Research. ,vol. 5, pp. 62- 81 ,(1967) , 10.1016/0008-6215(67)85008-0
G. Wolczunowicz, L. Bors, F. Cocu, Th. Posternak, Recherches dans la série des cyclitols, XLI. Synthèses de deux cyclopentane‐pentols Helvetica Chimica Acta. ,vol. 53, pp. 2288- 2295 ,(1970) , 10.1002/HLCA.19700530843
H. Z. Sable, Thelma Anderson, Bernadine Tolbert, Th. Posternak, Recherches dans la série des cyclitols XXXIII. Sur quelques cyclitols dérivés du cyclopentane Helvetica Chimica Acta. ,vol. 46, pp. 1157- 1165 ,(1963) , 10.1002/HLCA.19630460410
Rudolf Criegee, Oxydation ungesättigter Kohlenwasserstoffe mit Blei (4)‐salzen European Journal of Organic Chemistry. ,vol. 481, pp. 263- 302 ,(1930) , 10.1002/JLAC.19304810117
J. A. Franks, Bernadine Tolbert, Ruth Steyn, Henry Z. Sable, Studies on Cyclic Polyols. III. The Configurations and Reactions of Some Epoxydiols of Cyclopentane1,2 Journal of Organic Chemistry. ,vol. 30, pp. 1440- 1446 ,(1965) , 10.1021/JO01016A023
Harold R. Nace, Robert N. Iacona, The Reaction of 2α-Bromo-5α-cholestan-3-one with Dimethyl Sulfoxide Journal of Organic Chemistry. ,vol. 29, pp. 3498- 3503 ,(1964) , 10.1021/JO01035A012
Malcolm Korach, Donald R. Nielsen, Walker H. Rideout, Synthesis and Reactions of 3,4-Epoxycyclopentene Journal of the American Chemical Society. ,vol. 82, pp. 4328- 4330 ,(1960) , 10.1021/JA01501A050
Nathan Kornblum, Willard J. Jones, George J. Anderson, A NEW AND SELECTIVE METHOD OF OXIDATION. THE CONVERSION OF ALKYL HALIDES AND ALKYL TOSYLATES TO ALDEHYDES Journal of the American Chemical Society. ,vol. 81, pp. 4113- 4114 ,(1959) , 10.1021/JA01524A080