D phenylhydrazone

D-, phenylhydrazone, three modifications of, 124 D-, 6-phosphate, 94 D-, reverse aldolization of, 327 —, 2-acetamido-2-deoxy-n-, 85, 162, 196, 254-257, 259, 262, 305 —2-acetamido-2-deoxy-3-0-(/3-D-galac-topyranosyl)-D-, 305 —, 2-acetamido-2-deoxy-4-0- (jS-D-galac-topyranosyl)-D-, 306 —, 2-acetamido-l, 3,4,6-tetra-O-acetyl-2-deoxy-a, -D-, 196... 

Acetophenone similarly gives an oxime, CHjCCgHjlCtNOH, of m.p. 59° owing to its lower m.p. and its greater solubility in most liquids, it is not as suitable as the phenylhydrazone for characterising the ketone. Its chief use is for the preparation of 1-phenyl-ethylamine, CHjCCgHslCHNHj, which can be readily obtained by the reduction of the oxime or by the Leuckart reaction (p. 223), and which can then be resolved by d-tartaric acid and /-malic acid into optically active forms. The optically active amine is frequently used in turn for the resolution of racemic acids. 

D-Glucose phenylhydrazone [534-97-4] M 358.4, m 208 . Crystd from aqueous EtOH. 

Auf diese Weise erhalt man innerhalb 12 Stdn. 0,197 g (70% d. Th.), innerhalb 24 Stdn. 0,232 g (82% d.Th.) Benzaldehyd-2,4-dinitro-phenylhydrazon, dessen Menge auch innerhalb 36 Stdn. konstant bleibt. 

Auf ahnliche Weise erhalt man aus Hexansaure (0°) innerhalb 36 Stdn. 98% d.Th. He-xanal-2,4-dinitro-phenylhydrazon. 

Example CH=N-NHPh 1 CH = N—NHPh HOCH HCOH HCOH i ch2oh D-araib/no-Hexos-2-ulose bis(phenylhydrazone)... 

It was observed in those cases in which the oxidation was arrested too soon that an appreciable amount of silver chloride was deposited when the solution was concentrated. Furthermore, the mother liquor, when treated with phenyl-hydrazine in acetic acid, deposited some yellow crystalline D,L-mannose phenylhydrazone, m. p. 195-200° (Maquenne block). It is apparent that too vigorous oxidation results in the formation of hexoses. 

XXII, for which they proposed the alternative name 1-phenyl-D-fructo-sone reaction with o-phenylenediamine produced a crystalline compound to which they assigned the structure XXIV, that is, 2-(D-orobwo-tetrahy-droxybutyl)-3-pheuylquinoxaline, the substituted osone reacting in the open-chain form XXIII. Compound XXIV, on treatment with phenylhy-drazine, yielded crystalline 2-formyl-3-phenylquinoxaline phenylhydrazone... 

A strategy has been described for the synthesis of 2-ethyIthio-6-(3-hydroxy-1,2-0-isopropylidenepropyl)pteridin-4(3//)-one 90 which can be used as a useful intermediate for the conversion of neopterin to biopterin. Diaminopyrimidinone 86 reacts with D-arabinose phenylhydrazone 87, the obtained diastereomeric mixture 88 is converted into its isopropylidene derivative 89 which under oxidation conditions yields 90 <00H(53)1551>. 

In contrast to aldoses, ketoses, and compound 2, which, on treatment with phenylhydrazine, form phenylosazones, compound 4, under the same conditions, yields116 the phenylhydrazone of aldehydo-D-glucuronic phenylhydrazide (69). In a series of papers, Momose and coworkers117 120 described the synthesis of N-... 

Both L-gulose12,13 (9) and D-gulose (d-9, see Ref. 10) have been oxidized with bromine to L- or D-gulonic acid, respectively (see Scheme 1). L-Gulose (9) has been prepared by a number of different procedures. Schemes 2 and 3 show two early procedures that afforded L-gu-lose, but the overall yields were low (<30%). In the first procedure12 (see Scheme 2), D-glucitol (10) was converted into 2,4-O-benzylidene-D-glucitol (11), which was then oxidized with lead tetraacetate to 2,4-O-benzylidene-L-xylose (12). Nitromethane was added to 12 to afford crystalline 13 in 50% yield. Hydrolysis of 13 provided 14, which was treated with sodium hydroxide, followed by sulfuric acid, to afford 9, which was isolated in 52% yield as the 2-benzyl-2-phenylhydrazone. 

T.J. Thurston, R.G. Brererton, D.J. Foord, R.E.A. Escott, Principal components plots for exploratory investigation of reactions using ultraviolet-visible spectroscopy application to the formation of benzophenone phenylhydrazone, Talanta, 63, 757-769 (2004). 

Erleidet das Phenylhydrazon 98 die Amadori-Umlagerung zu 107 oder bildet sich zunachst ein Anil 109 und daraus unter Amadori-Umlagerung 1111 Letzteren Verlauf glauben Micheel und Dijong bewiesen zu haben 1 D. 

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