Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been f...
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| Autores principales: | , , , |
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| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v7_n4_p395_Cerezo |
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| Sumario: | NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been found that, in all cases, acyclic (1) and cyclic (2, 3) products are formed simultaneously. The molar ratio of the cyclic products formed (2+3) to the acyclic ones (1) is higher if the acyl group is aliphatic. The yield ofN-benzoyl-β-D-mannopyranosylamine obtained in the ammonolysis of penta-O-benzoyl-D-mannopyranose is higher than that ofN-benzoyl-β-D-glucopyranosylamine from penta-O-benzoyl-D-glucopyranose, showing the influence of inversion of configuration at C-2. This influence is less pronounced for other acylated monosaccharides that belong to themanno series. © 1968 Elsevier Publishing Company, Amsterdam. |
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