Glucose hydrochloride

Carbohydrate Components of Antibiotics. Part III. Synthesis of 3.6-Dideoxy-3-dimethylamino- 3-D-glucose Hydrochloride Monohydrate the Absolute Configuration of Mycaminose, A. B. Foster, T. D. Inch, J. Lehmann, M. Stacey, and J. M. Webber, /. Chem. Soc., (1962) 2116-2118. 

Another main subject of research of Garcia Gonzalez, with the collaboration of J. Femandez-Bolanos, was the reaction of amino sugars with isothiocyanic acid derivatives. 2-Amino-2-deoxy-D-glucose hydrochloride and potassium thiocyanate were shown to give rise to 4-(D-arabino-tetritol-l-... 

Praparative Herstellung von Krist. 6-Desoxy-6-amino-D-glucose-hydrochlorid und Konstitution einiger Zwischenprodukte, by E. Hardegger, G. Zanetti, and K. Steiner, Helv. Chim. Acta, 46 (1963) 282-287. 

The protonated amino group, however, has no nucleophilic activity, and does not form a hemiacetal an amino sugar can, therefore, be obtained, as a salt, in an otherwise unfavorable form. For example, 6-amino-6-deoxy-L-sorbose can be isolated as the hydrochloride of a furanose form (22) (presumably a). In alkaline solution, immediate ring-expansion to the pyranose form (23) occurs127 this reaction can be reversed under strongly acidic conditions. 4-Amino-4,6-dideoxy-D-glucose hydrochloride forms a 35 65 mixture of the a- and / -pyranose forms in solution.128... 

Amino-2-deoxy-D-glucose hydrochloride (15 g, 69.6 mmol) is dissolved in fuming hydrochloric acid (concentrated hydrochloric acid saturated with hydrogen chloride at 0°C, 120 mL), propane-l,3-room temperature for 3 days. Ethanol is added, the solution neutralized with lead carbonate, and the salts filtered. Evaporation affords a solid, which is recrystallized from ethanol-watef-ether (18 g, 84%) mp 204-206°C, [a]D —8.9° (c 1.45, water). 

The direct one-step preparation of 2-acetamido-3,4,6-tri-0-acetyl-2 -deoxy-a-D-glu copyranosyl chloride was reported by Micheel and co-workers,3 and the described procedure is essentially the method of Horton and Wolfrom.4 The product was first prepared through a two-step route from 2-amino-2-deoxy-D-glucose hydrochloride by Baker and co-workers,5 and a number of adaptations of this method have been described6-8... 

In the second synthesis, in which the / 1,6-linked disaccharide was prepared first and the substituents introduced afterwards, 2-amino-2-deoxy-glucose hydrochloride was transformed into the well known (16)... 

Difficulties are encountered in carrying out controlled, partial hydrolyses of chitin because of the need to use concentrated acids to dissolve the polysaccharide. Chitosan (de-A -acetylated chitin), however, is water-soluble and amenable to controlled hydrolysis. Using ion-exchange chromatography, a chitosan hydrolyzate has been fractionated to give at least five saccharides, the first two of these having been characterized as 2-amino-2-deoxy-D-glucose hydrochloride and chitobiose hydrochloride. > Fractionation of chitosan hydrolyzates on oarbon-Celite was only successful after selective A-acetylation and then it yielded the first seven members of a series of chitin saccharides, the properties of which clearly indicate the... 

Amino-6-deoxy-D-glucose hydrochloride 2-Benzamido-2-deoxy-D- ethyl 119-121 -25.5 water 45... 

The isolation of D-aroWno-hexulose phenylosazone from both 1,4-anhydro-D-mannitol and 1,5-anhydro-D-glucitol indicates that o-aroMno-hexosulose is among the reaction products. - Crude methyl D-glucofurano-sides in dilute sulfuric acid yield pyruvaldehyde, and 2-amino-2-deoxy-D-glucose hydrochloride suffers oxidative deamination. ... 

The reactions of amino glycoses with a variety of jS-dicarbonyl compounds have been studied systematically in aqueous acetone solution at neutral pH and room temperature. Under these conditions, well defined products are obtained, sometimes in yields as high as 90-100%. Using this technique, 2-amino-2-deoxy-D-glucose hydrochloride, plus the equivalent amounts of sodium carbonate and ethyl acetoacetate, gives a product (m.p. 142-143°, [a]D —25°) different from that obtained by Pauly and... 

The reaction of amino sugars with (8-dicarbonyl compounds in alkaline solution produces (tetrahydroxybutyl) pyrroles together with simpler pyrrole compounds lacking the tetrahydroxybutyl side-chain. 2-Amino-2-deoxy-D-glucose hydrochloride and ethyl acetoacetate, heated in aqueous solution at pH 9.7, give a mixture of ethyl 2-methyl-5-(D-ara )mo-tetra-hydroxybutyl)pyrrole-3-carboxylate (1) and ethyl 2-methylpyrrole-3-carboxylate. The yields of these compounds are in the approximate ratio... 

The product formed from the oxidative condensation of 2-amino-2-deoxy-D-glucose hydrochloride with o-phenylenediamine is 2(d-ar imo-tetrahydroxybutyl)quinoxaline (42) and not the alternate formulation (43). The spectrum of the quinoxaline in dimethyl... 

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