125948-63-2

Upstream product

• 600-14-6 2,3-Pentanedione 
• 113-24-6 sodium pyruvate 
• 107-02-8 acrolein 

Downstream Products

• 160666-92-2 (S)-2-benzoyloxypentan-3-one 
• 164145-56-6 (2S,4R,5R)-2-benzoyloxy-5-hydroxy-4-methylpentan-3-one 
• 1352831-83-4 (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one 
• 177905-43-0 Benzoic acid (E)-(1S,3R,4S,5R)-5-fluoro-4-hydroxy-1,3,5-trimethyl-2-oxo-dec-7-enyl ester 
• 177905-42-9 Benzoic acid (E)-(1S,3R,4R,5S)-4-hydroxy-1,3,5-trimethyl-2-oxo-dec-7-enyl ester 
• 207680-82-8 Benzoic acid (1S,3R,4R,5S)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-2-oxo-hexyl ester 
• 207680-83-9 (2S,4R,5R,6R)-2-benzoyloxy-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one 
• 207680-79-3 (2S,4R,5R,6R)-7-(benzyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate 
• 207680-85-1 (2S,3R,4S,5R,6S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-2,3-diol 
• 207680-86-2 (2S,3R,4S,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-2,3-diol 
• 173726-06-2 (2S,4R,5R,6E)-2-benzoyloxy-5-hydroxy-4-methyloct-6-en-3-one 

Relevant academic research and scientific papers

Promiscuous substrate binding explains the enzymatic stereoand regiocontrolled synthesis of enantiopure hydroxy ketones and diols

Regio- and stereoselective reductions of several diketones to afford enantiopure hydroxy ketones or diols were accomplished using isolated alcohol dehydrogenases (ADHs). Results could be rationalised taking into account different (promiscuous) substrate-binding modes in the active site of the enzyme. Furthermore, interesting natural cyclic diketones were also reduced with high regio- and stereoselectivity. Some of the 1,2 and 1,3-diketones used in this study were reduced by employing a low excess of the hydrogen donor (2-propanol) due to the quasi-irreversibility of these ADH-catalysed processes. Thus, using lower quantities of co-substrate, scale-up could be easily achieved.

Enantiogenic synthesis of (R)-(-)-3-hydroxy-1-penten-4-one

Condensation of pyruvate and acrolein with whole cells of baker's yeast resulted in a mixture of 3-hydroxy-1-penten-4-one 1 and 4-hydroxy-1-penten-3-one 2. The absolute configuration (R) and the enantiomeric excess (ee 72%) of the compound 1 were determined.