Condensation of al-forms of sugars with pyridine salts containing an active N-methylene group
A crotonaldehyde type of condensation takes place in acetic anhydride between phenacylpyridinium iodide and al-D-glucose or al-D-galactose, to give mono-products, while al-D-mannose heptaacetate gives a di-product. If the heating time is increased, al-D-galactose is also found to give a di-product. Condensation of al-D-glucose with p-nitrolylpyridinium iodide in ethanol in the presence of pyridine gives a mono-product. In ethanol, the iodides obtained react with Ba (ClO4)2 to give perchlorates, deacetylated by perchloric acid in methanol.
KeywordsAcetic Methanol Sugar Organic Chemistry Pyridine
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- 1.Yu. A. Zhdanov, G. V. Bogdanova, and V. G. Zolotukhina, DAN, 157, 917, 1964.Google Scholar
- 2.Yu. A. Zhdanov and G. V. Bogdanova, KhGS [Chemistry of Heterocyclic Compounds], p. 56, 1966.Google Scholar
- 3.F. Kröhnke, Angew Chem., 75, 4, 181, 1963.Google Scholar
- 4.F. Kröhnke, Angew Chem., 65, 617, 1953.Google Scholar
- 5.K. Dickore and F. Kröhnke, Angew Chem., 93, 1072, 1960.Google Scholar
- 6.P. N. Kovalenko and K. N. Bagdasarov, Physicochemical Methods of Analysis [in Russian], Rostov-on-Don State University Press, p. 243, 1962.Google Scholar
- 7.V. I. Esafov, Zav. lab., 21, 1160, 1955.Google Scholar
- 8.F., King, J. Am. Chem. Soc., 66, 894, 1944.Google Scholar