67800-61-7

Upstream product

• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 102036-15-7 (R,S)-2-butanoyloxy-3-chloropropyl p-toluenesulfonate 
• 102129-99-7 (R,S)-2-hydroxy-3-chloropropyl p-toluenesulfonate 
• 141-75-3 butyryl chloride 
• 102036-16-8 (R,S)-2-acetoxy-3-chloropropyl p-toluenesulfonate 
• 104-15-4 toluene-4-sulfonic acid 
• 113826-06-5 (R)-glycidyl tosylate 

Downstream Products

• 67843-74-7 (S)-epichlorohydrin 
• 51594-55-9 (R)-(-)-epichlorohydrin 

Relevant academic research and scientific papers

Immobilization of lipase from Burkholderia cepacia into calcium carbonate microcapsule and its use for enzymatic reactions in organic and aqueous media

We disclosed a useful procedure for the immobilization of a lipase from Burkholderia cepacia based on its encapsulation into vaterite calcium carbonate microcapsule. The immobilized enzyme had an adequate activity for the hydrolysis of 4-nitrophenyl aceta

Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates.

Preparation of optically active 1,2-diol monotosylates by enzymatic hydrolysis

An easy preparation of optically active 1,2-diol monotosylate derivatives by enzymatic hydrolysis is disclosed. Lipase PS (Burkholderia cepacia) catalyzes the hydrolysis of racemic 2-acetoxyhexyl tosylate with excellent enantioselectivity to afford the corresponding optically active compounds. In this reaction, a unique temperature effect is observed. After optimizing the reaction conditions, this procedure is widely applicable to the practical preparation of both enantiomers of various optically active compounds with high ee. Georg Thieme Verlag Stuttgart.

Selective Additions of Gaseous Hydrochloric Acid to Crystalline Epoxides und Steroid-Epoxides

Solid epoxides add gaseous HCl or KBr regioselectively and without melting, if the melting points are sufficiently high.Such additions proceed diastereoselectively with chiral epoxides.These gas/solid reactions are compared to similar transformations in solution.One observes interesting reaction sequences in the conversions of steroidal epoxides.Thus the opening of the epoxide ring may be followed by cationic rearrangements, or it occurs elimination od water, if it creates conjugation to a carbonyl group.

A Convenient Chemoenzymatic Synthesis of (R)- and (S)-(Chloromethyl)oxirane

(R)- and (S)-1-Chloro-3-tosyloxypropan-2-ol have been prepared by biocatalysed enantioselective esterification in hexane, and in turn could be readily converted into optically active (chloromethyl)oxirane in high yield.

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.

Lipase-catalyzed Stereoselective Hydrolysis of 2-Acyloxy-3-chloropropyl p-toluenesulfonate

Lipase-catalyzed stereoselective hydrolysis of 2-acyloxy-3-chloropropyl p-toluenesulfonate (1) was investigated.From the screening tests, lipases from Pseudomonas aeruginosa, Aspergillus niger, Mucor species, Rhizopus delemar and Rhizopus japonicus were f

Synthesis of (R,S)-(5Z,8E,10E)-12-Hydroxyheptadeca-5,8,10-trienoic Acid and of (R,S) and (S)-(5Z,8Z,10E,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoic Acid and their Racemic 5,6,8,9-tetradeuterioisomers

(5Z,8Z,10E,14E)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acid , (R,S)-(5Z,8Z,10E,14Z)-12-hydroxy-5,6,8,9-tetradeuterio-5,8,10,14-tetraenoic acid, (R,S)-(5Z,8E,10E)-12-hydroxyheptadeca-5,8,10-trienoic acid, and (R,S)-(5Z,8E,10E)-12-hydroxy-5,6,8,9-tetradeuterioheptadeca-5,8,10-trienoic acid have been prepared by total synthesis.Deuterium was introduced at selected sites by partial reduction.All the acids were prepared from the common intermediate ethyl 10,10-diethoxydeca-5,8-dienoate.The c.d. spectrum of (S)-(7h) confirmed its identity with the natural product.The mechanism of the reaction of heptynyl-lithium with (S)-1-chloro-2,3-epoxypropane has been shown to be by attack on the epoxide group, with subsequent recyclisation of the chloroalkoxide to give (S)-1,2-epoxydec-4-yne.