127911-73-3

Upstream product

• 127840-21-5 Butyric acid 1-(toluene-4-sulfonyloxymethyl)-undecyl ester 
• 2538-64-9 1,2-dodecanediol bisbutyrate 
• 1119-87-5 dodecane-1,2-diol 
• 606939-39-3 1-hydroxydecane-2-yl acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 85514-84-7 (2R)-dodecane-1,2-diol 

Downstream Products

• 1094023-95-6 (2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-benzenesulfonyloxy)dodecane 
• 109856-85-1 (R)-1,2-epoxydodecane 

Relevant academic research and scientific papers

Lipase-catalyzed stereoresolution of long-chain 1,2-alkanediols: A screening of preferable reaction conditions

Scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediol enantiomers via stereoselective cleavage of esters was developed. The influence of lipase, reaction medium, nucleophile, temperature and the structure of the acyl group on the reaction velocity, the stereopreference and the stereoselectivity of the deacylation was studied. In addition, the rate of the spontaneous intramolecular migration of different acyl groups was determined for the intermediate 2-monoesters. The acyl group migration may diminish the apparent stereoselectivity of the two-step process if fast migrating acyl groups are used. It was found that the migration rate of different acyl groups differs by up to two orders of magnitude, being faster for acetyl and isobutyryl and much slower for butyryl and benzoyl groups. The best results were obtained by the sequential methanolysis of bis-butyryl-1,2-alkanediols in an acetonitrile/methanol mixture catalyzed by Candida antarctica lipase B (CALB) at 20 °C, affording (S)-1,2-alkanediols. Stereo- and chemoselective crystallization of the deacylated (S)-1,2-alkanediols from the reaction mixture complements the enzymatic process improving the stereochemical purity to up to ee > 99.8%. (R)-1,2-Alkanediol 2-monoesters were separated from the mother liquor and enriched stereochemically by repeated incubation with CALB, then separated, hydrolyzed with alkali and crystallized to afford (R)-alkanediols of ee > 99.8%.

Synthesis of amphiphilic amino alcohols

An efficient and general approach for the synthesis of amphiphilic 1,2-amino alcohols is reported. The use of N-benzyl protecting groups is essential for obtaining good yields when opening a long-chain terminal epoxide with an amine. Copyright Taylor & Francis Group, LLC.

A CHEMOENZYMATIC ACCESS TO OPTICALLY ACTIVE 1,2-EPOXIDES

Lipase-catalyzed transacylation in organic media was employed to produce optically active α-hydroxy tosylate which could be readily converted to the corresponding 1,2-epoxides with high optical purity.