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Zur Synthese von 1‐Alkylamino‐1‐desoxy‐ D ‐fructosen. 3. Mitteilung über Aminozucker
Author(s) -
Huber G.,
Schier O.,
Druey J.
Publication year - 1960
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19600430315
Subject(s) - chemistry , hydrogenolysis , alkyl , stereochemistry , fructosamine , anomer , catalysis , medicinal chemistry , organic chemistry , medicine , insulin , endocrinology
With alkylbenzylamine D ‐glucose undergoes A MADORI ‐rearrangement to 1‐alkyl‐benzylamino‐1‐deoxy‐ D ‐fructose. Catalytic hydrogenolysis of the benzyl group gives rise to 1‐alkylamino‐1‐deoxy‐ D ‐fructose (alkyl‐fructosamine). In this way, the methyl, ethyl and butyl derivatives of fructosamine have been prepared in crystalline form. With isocyanic acid and rhodanic acid the 1‐alkylamino‐1‐deoxy‐ D ‐fructoses are converted into imidazole derivatives, as expected for substances of the α‐aminoketone type.