96938-07-7

Upstream product

• 96938-12-4 1-p-Tolylsulfanyl-pentadecan-2-ol 
• 18633-25-5 1,2-epoxypentadecane 
• 158627-95-3 (R)-1-chloro-pentadecan-2-ol 
• 2765-11-9 n-pentadecanal 
• 96938-04-4 1-((R)-Toluene-4-sulfinyl)-pentadecan-2-ol 
• 96937-99-4 1-((R)-Toluene-4-sulfinyl)-pentadecan-2-one 
• 15890-72-9 laurylmagnesium bromide 

Downstream Products

• 158627-97-5 2-((R)-2-Hydroxy-pentadecyl)-6-methoxy-N-methyl-benzamide 
• 1187560-47-9 C₂₁H₃₆OS 
• 259799-91-2 (R)-3-hydroxyhexadecanenitrile 
• 928-17-6 (R)-β-hydroxypalmitic acid 
• 83780-74-9 (S)-(+)-3-hydroxyhexadecanoic acid 
• 158627-98-6 2-((S)-2-Hydroxy-pentadecyl)-6-methoxy-N-methyl-benzamide 
• 1309462-96-1 C₂₄H₃₉NO₃S 
• 1309463-10-2 6-(S)-t-butyldimethylsilyloxy-4-isocyano-4-tosylnonadecane 
• 1309462-98-3 3-(S)-t-butyldimethylsilyloxy-1-isocyano-1-tosylhexadecane 

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.

Termination of the structural confusion between plipastatin A1 and fengycin IX

Plipastatin A1 and fengycin IX were experimentally proven to be identical compounds, while these had been considered as diastereomers due to the permutation of the enantiomeric pair of Tyr in most papers. The 1H NMR spectrum changed to become quite similar to that of plipastatin A1, when the sample which provided resembled spectrum of fengycin IX was treated with KOAc followed by LH-20 gel filtration. Our structural investigations disclosed that the structures of these molecules should be settled into that of plipastatin A1 by Umezawa (l-Tyr4 and d-Tyr10).

Synthesis of aculeatins A and B via iterative hydrolytic kinetic resolution

A simple and concise approach for the synthesis of aculeatins A and B starting from (±)-epichlorohydrin is described. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution and a Linchpin coupling as key steps. Georg Thieme Verlag Stuttgart.

Polyol synthesis with β-Oxyanionic alkyllithium Reagents: Syntheses of aculeatins A, B, and D

Synthesis of ketone aldol products using a non-aldol route was developed. The β-phenylthio alcohols were prepared from optically pure oxiranes. Deprotonation and reductive lithiation generated the key intermediate, a β-oxyanionic alkyllithium reagent. Addition to a Weinreb amide produced the β-hydroxy ketone In >90% yield using only 1.5 equiv of the phenylthio alcohol. Stereoselective reduction of the ketone led to either the syn-or anti-1,3-diol. This simple, convergent sequence was used to prepare aculeatins A, B, and D from a common intermediate

Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76

EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8% overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze - Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.

Isolation, Structure Determination and Synthesis of New Dihydroisocoumarins from Ginkgo biloba L.

New optically active 8-hydroxy-3-alk(en)yl-3,4-dihydroisocoumarins 2a-c were isolated from Ginkgo biloba L. fruits.The absolute configuration was determined to be R by comparison with both enantiomers of the 8-hydroxy-3-tridecyl-3,4-dihydroisocumarin synthesized from optically active epichlorhydrins.

REDUCTION OF β-HYDROXYSULFOXIDES: APPLICATION TO THE SYNTHESIS OF OPTICALLY ACTIVE EPOXIDES

β-hydroxysulfoxides of opposite stereochemistry can be prepared in very high diastereoisomeric excesses (90 to 95 percent) by reduction of β-ketosulfoxides with DIBAL or DIBAL/ZnCl2.A very efficient method to transform these reduction products into optically active epoxides is also described.