DL-Glyceraldehyde

HC CH(0H) CH20H. optically active. D-glyceraldehyde is a colourless syrup. May be prepared by mild oxidation of glycerol or by hydrolysis of glyceraldehyde acetal (prepared by oxidation of acrolein acetol). DL-glyceraldehyde forms colourless dimers, m.p. IBS-S C. Converted to methylglyoxal by warm dilute sulphuric acid. The enantiomers... 

The imidazoles formed in the reaction of aqueous ammonia with other a-hydroxycarbonyl compounds, for example, the triose DL-glyceraldehyde, and such a-dicarbonyl compounds as 3-deoxy-D-glycero-pentosulose (59), and the 3,6-dideoxy-L-erythro-, D-arabino-, and 3-deoxy-D-erytforo-hexosuloses (60, 61, and 62), respectively, are summarized in Table VIII for reactions in which formaldehyde was added, and in Table IX for reactions in which it was not added. 

Iron(III)hydroxide oxide [Fe(0H)0] has been shown to catalyze the condensation of 25-mM DL-glyceraldehyde to ketohexoses at 15 °C (pH 5-6). After 16 days 15.2% of sorbose, 12.9% of fructose, 6.1% of psicose, 5.6% of tagatose, and 2.5% of dendroketose are obtained. After 96 days at 15 °C this mixture was not decomposed. [Fe(0H)0] also catalyzes the isomerization of glyceraldehyde into dihydroxy acetone and of dihydroxy acetone into lactic acid [41]. 

Cytoxazone is a novel cytokine modulator. The total synthesis of this natural product and its enantiomer was accomplished by S. Sugiyama. The 3-amino-1,2-propanediol moiety was synthesized by a Petasis boronic acid-Mannich reaction between DL-glyceraldehyde, (R)-1-(1-naphthyl)ethylamine and 4-methoxyphenylboronic acid to provide a 1 1 mixture of the diastereomeric products. The diastereomers could be separated at a later stage in the synthesis and transformed into (-)- and (+)-cytoxazone. 

I rcpMicil hy hiMlIn ii mixluic of l.l imilcx ol phosphoiyl chloridu imil 2 inolcs uf phenol lo 180 iind distilling the product. It is used Tor the preparation of dl-glyceraldehyde 3-phosphoric acid, and dihydroxyacetone phosphate," and diphenyl-... 

Under conditions similar to those under which cyclohexene affords cis-cyclo-hexane-l,2-diol in yield of 30-33%, Evans et obtained DL-glyceraldehyde diethyl acetal from acrolein diethyl acetal in 67% yield. A suspension of the acetal... 

Properties (DL-glyceraldehyde.) Tasteless crystals from alcohol-ether mixture. Mp 145C. Insoluble in benzene, petroleum ether, pentane. 

DL-Glyceraldehyde, known, in contrast to the optically active forms, as a crystalline material (dimer, mp 142°), has been resolved by condensation with (d Xtro)-a-(2-hydroxy-1 -naphthyl jbenzylamine.16... 

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