Acetal dihydroxyacetone

When dihydroxyacetone is heated in aqueous solution with cupric acetate, the product is chiefly oxomalonic acid. Evans and Waring, J. Am. Chem. Soc. 48, 2680 (1926). 

The original preparation of 6-C-perfluoroalkyl-D-fructose has been reported. The first step of this synthesis is the perfluoroalkylation of acrolein acetal. The key step of the synthesis is an aldol condensation between D-3-fluoroalkylglyceraldehyde and dihydroxyacetone phosphate, with RAMA as biocatalyst (RAMA is an aldolase found in rabbit muscles) (Figure 6.43). ... 

Research Focus Synthesis of polycarbonates, poly(acetal carbonate)s, poly(spiroacetal)s, polyesters, and polyurethanes using dihydroxyacetone. 

The bismethylenedioxy group (BMD) [ (49)] represents the most suitable protecting group for the dihydroxyacetone side chain of corticosteroids. This group is stable to lead tetraacetate, brief heating with hydrochloric acid in acetic acid,108 or with sulfuric acid in methanol18 and to Jones oxidation.189... 

Intermolecular Nucleophilic Substitution with Heteroatom Nucleophiles. A patent issued in 1965 claims substitution for fluoride on fluorobenzene-Cr(CO)3 in dimethyl sulfoxide (DMSO) by a long list of nucleophiles including alkoxides (from simple alcohols, cholesterol, ethylene glycol, pinacol, and dihydroxyacetone), carboxylates, amines, and carbanions (from triphenyhnethane, indene, cyclohexanone, acetone, cyclopentadiene, phenylacetylene, acetic acid, and propiolic acid). In the reaction of methoxide with halobenzene-Cr(CO)3, the fluorobenzene complex is ca. 2000 times more reactive than the chlorobenzene complex. The difference is taken as evidence for a rate-limiting attack on the arene ligand followed by fast loss of halide the concentration of the cyclohexadienyl anion complex does not build up. In the reaction of fluorobenzene-Cr(CO)3 with amine nucleophiles, the coordinated aniline product appears rapidly at 25 °C, and a carefiil mechanistic study suggests that the loss of halide is now rate limiting. 

Polysorbate 20, Fragrance. Tocophery Acetate (Vitamin E Acetate), tmidazolidinyl Urea, Dihydroxyacetone. 

Aldehydes have been formed from alcohols by the use of other oxidizing agents. Dihydroxyacetone has been oxidized with excess cupric acetate to hydroxypyruvic aldehyde in 87% yield. p-Cyanobenzyl alcohol treated at 0° with a chloroform solution of nitrogen tetroxide gives practically pure p-cyanobenzaldehyde (90%). Aromatic alcohols containing nitro groups have been oxidized to the corresponding nitro aldehydes with concentrated nitric acid, e.g., o- and p-nitrobenzaldehydes (80-85%). m-Nitrobenzenesulfonic acid in basic media has been used for the oxidation of substituted benzyl alcohols, most satisfactorily for the water-soluble phenolic benzyl alcohols. Selenium dioxide, or less effectively tellurium dioxide, oxidizes benzyl alcohol slowly to benzaldehyde. ... 

Oxidation of ingested alcohol produces acetaldehyde, acetate, and NADH. A high NADH/NAD+ ratio slows the TCA cycle and promotes the synthesis of glycerol 3-phosphate from dihydroxyacetone phosphate. Fatty acid synthesis is stimulated and, because of the effects of ethanol on mitochondria, fatty acid oxidation is decreased. The net result is that fatty acids react... 

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