130404-10-3

Upstream product

• 3234-28-4 1,2-epoxytetradecane 
• 1120-36-1 1-tetradecene 
• 124-25-4 myristylaldehyde 

Downstream Products

• 1004752-64-0 C₂₄H₄₀O₃S 
• 153062-86-3 (R)-tetradecane-1,2-diol 
• 153062-87-4 (S)-tetradecane-1,2-diol 
• 1004311-46-9 C₂₄H₄₁NO₃ 
• 1004311-45-8 C₂₄H₃₉NO₂ 
• 1004311-49-2 C₃₅H₅₃NSO₈ 
• 1004311-48-1 C₂₈H₄₇NO₆ 
• 1004311-47-0 C₂₈H₄₅NO₄ 

Relevant academic research and scientific papers

Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones

3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

Shell cross-linked micelle-based nanoreactors for the substrate-selective hydrolytic kinetic resolution of epoxides

Shell cross-linked micelles (SCMs) containing Co(III)-salen cores were prepared from amphiphilic poly(2-oxazoline) triblock copolymers. The catalytic activity of these nanoreactors for the hydrolytic kinetic resolution of various terminal epoxides was investigated. The SCM catalysts showed high catalytic efficiency and, more significantly, substrate selectivity based on the hydrophobic nature of the epoxide. Moreover, because of the nanoscale particle size and the high stability, the catalyst could be recovered easily by ultrafiltration and reused with high activity for eight cycles.

A concise synthesis of (-)-deoxoprosopinine

A simple and highly efficient approach to (-)-deoxoprosopinine from racemic epoxide as a starting material is described employing a Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless asymmetric dihydroxylation (AD) as key steps. Georg Thieme Verlag Stuttgart.

Stereochemistry of Δ4 dehydrogenation catalyzed by an ivy (Hedera helix) Δ9 desaturase homolog

The stereochemistry of palmitoyl-ACP Δ4 desaturase-mediated dehydrogenation has been examined by tracking the fate of deuterium atoms located on stereospecifically monodeuterated substrates-(4S)- and (4R)-[4-2H1]-palmitoyl-ACP and (5S)- and (5R)-[5- 2H1]-palmitoyl-ACP. It was found that the introduction of the (Z)-double bond between C-4 and C-5 of a palmitoyl substrate occurs with pro-R enantioselectivity - a result which matches that obtained for a closely related homolog-castor stearoyl-ACP Δ9 desaturase. These data show that despite the difference in regioselectivity between the two enzymes, the stereochemistry of hydrogen removal is conserved. The Royal Society of Chemistry.

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.

A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts

Non-racemic terminal long-chain alkyl epoxides are prepared from racemic epoxides and 1 mol% (R,R)- and (S,S)-salen(Co)III catalysts following a modified procedure for kinetic resolution. The ee's for all epoxides (C-10, C-12, C-14, C-16, C-18, C-20) exceed 95% and the chemical yields range from 85% to 95%.