13269-77-7Relevant articles and documents
An improved synthesis of phosphonomethyl analogues of glyceraldehyde-3-phosphate and dihydroxy-acetone phosphate
Page,Blonski,Perie
, p. 8027 - 8030 (1995)
Compounds 1 and 2, phosphonate analogues of dihydroxy-acetone phosphate (DHAP) and glyceraldehyde-3-phosphate (GAP) respectively, are easily and quantitatively obtained from diethyl-4,4-diethoxy-3-hydroxybutyl-1-phosphonate 3. Depending upon the acidic conditions utilised for the deprotection of the phosphonate and carbonyl groups, the aldol/ketol rearrangement allows the synthesis of either compound.
Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses
Camps Bres, Flora,Guerard-Helaine, Christine,Fernandes, Carlos,Castillo, Jose A.,Lemaire, Marielle
, p. 1175 - 1181 (2013/10/08)
Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA.
Stereoselectivity of Baker's yeast reduction of 2-propanones: influence of substituents.
Waagen,Partali,Hollingsaeter,Huang,Anthonsen
, p. 506 - 510 (2007/10/02)
The stereoselectivity of Baker's yeast reduction of prochiral alpha-oxygenated 2-propanones has been studied by varying the substrate structure. The 1-hydroxy-3-methoxy-3-propanone 1a was reduced to the corresponding alcohol (R)-2a with 88% enantiomeric excess. Replacing the hydroxy group in 1a with phenoxy or benzyloxy (1b and 1c) gave the alcohols (S)-2b and (S)-2c with 53 and 32% ee, respectively. Reduction of the methyl ketone 1d gave the alcohol (S)-2d with 91% ee. Attempts to improve the enantioselectivity of the reduction of 1c by lowering the substrate concentration or addition of selective reductase inhibitors had only small effect on the enantioselectivity.
