85617-06-7

Upstream product

• 138298-66-5 (2R,3R)-3-((undecan-2-yl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester 
• 112-12-9 methyl nonyl ketone 
• 1653-30-1 undecan-2-ol 
• 112-31-2 caprinaldehyde 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 138298-65-4 (4R,5R)-2-nonyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 544-97-8 dimethyl zinc(II) 
• 138381-36-9 (2R,3R)-3-((undecan-2-yl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester 

Relevant academic research and scientific papers

Enzymatic chemical transformations of aldehydes, ketones, esters and alcohols using plant fragments as the only biocatalyst: Ximenia americana grains

The present study demonstrated the ability of Ximenia american as a biocatalyst in reduction, hydrolysis and esterification reactions. The reduction reactions of aldehydes and ketones, ester hydrolysis and esterification of alcohols were carried out with interesting results. Reduction of ketones afforded yields of 6–60% with ee in the range of 35–>99% and that of aldehydes in yields of 51–99%. On the other hand, ester hydrolysis afforded yields of 58–98% with ee in the range 34–87%, while esterification of alcohols in 18–99% yields. Experimental conditions for all reactions have been defined using standard substrates as indicated in results and discussion. Some of the products are the potential building blocks for the synthesis of molecules which are of pharmaceutical and agrochemical importance.

Identification of an ε-keto ester reductase for the efficient synthesis of an (R)-α-lipoic acid precursor

Abstract A novel reductase (CpAR2) with unusually high activity toward an ε-keto ester, ethyl 8-chloro-6-oxooctanoate, was isolated from Candida parapsilosis. The asymmetric reduction of ethyl 8-chloro-6-oxooctanoate using Escherichia coli cells coexpressing CpAR2 and glucose dehydrogenase genes gave ethyl (R)-8-chloro-6-hydroxyoctanoate, a key precursor for the synthesis of (R)-α-lipoic acid, in high space-time yield (530 gL-1d-1) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10-L scale. This method provides a greener and more cost-effective method for the industrial production of (R)-α-lipoic acid.

Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol and its propionate, the sex pheromones of pine sawflies

The stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (diprionol) and its propionate, the sex pheromones of pine sawflies (Neodiprion sp. and other), in high enantiomeric purity was achieved from (1R,3S)-2,2-dichloro-3-methylcyclopropane

Lentinus strigellus: a new versatile stereoselective biocatalyst for the bioreduction of prochiral ketones

Growing cells of the basiodiomycete Lentinus strigellus in potato-dextrose broth have been used for the first time as a biocatalyst in the stereoselective reduction of aromatic and aliphatic ketones. Most of the aromatic ketones were converted into the corresponding optically active alcohols in up to >99% enantiomeric excess under very mild reaction conditions. Among the aliphatic ketones tested, 2-octanone was enzymatically reduced by this microorganism to enantiopure (S)-2-octanol with almost complete conversion.

Mechanistic investigation of the Candida albicans CCT 0776 stereoinversion system and application to obtain enantiopure secondary alcohols

Phenylethanol deracemization with Candida albicans CCT 0776 whole cells yields the (R)-enantiomer in over 99% enantiomeric excess and 98% yield. The deracemization process involves, in the first step, a fast, highly (S)-selective oxidation (NADP and O2 dependent) and, in the second step, a slower partially (S)-selective reduction (NADH dependent) of the intermediate ketone. The process was extended to other 2-alkanols, 1,2-diols and 1,3-diols and, with the exception of 1,3-diol (unreactive), the enantiomeric excess and yield of the deracemization were about 99% and 62-98%, respectively.

Enantioselective addition of dimethylzinc to aldehydes catalyzed by N-substituted mandelamide-Ti(IV) complexes

Amides derived from (S)-(+)-mandelic acid in the presence of titanium isopropoxide catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes with good yields and ee up to 90%.

Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission

Johnson-type acetals derived from dimethyl tartrate give, after opening with Me2BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting bromo acetal through an invertive and temperature-dependent process. The acetals are prepared by reaction of the desired aldehyde with dimethyl tartrate. Removal of the auxiliary is accomplished through Sml2 reduction or by an addition - elimination protocol using methoxide.

Stereoselective opening of acetals derived from dimethyl tartrate

Acetals of dimethyl tartrate can be used to prepare optically active secondary alcohols from the corresponding aldehydes. The key step involves treatment of the acetals with dialkylboron bromides and higher order cuprates. The process involves an unusual