103775-63-9

Upstream product

• 108-05-4 vinyl acetate 
• 32464-98-5 toluene-4-sulfonic acid 2-hydroxypropyl ester 
• 103745-04-6 2-acetoxypropyl tosylate 
• 108-24-7 acetic anhydride 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 64-19-7 acetic acid 

Downstream Products

• 790695-53-3 methyl 4-{[(2S)-2-acetoxypropyl]oxy}-2-(trifluoromethyl)benzoate 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 

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.

4,4-DIFLUORO-1,2,3,4-TETRAHYDRO-5H-1-BENZAZEPINE DERIVATIVE OR SALT THEREOF

A novel 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or a pharmaceutically acceptable salt thereof, which is useful as an agent for treating or preventing nocturia and/or diabetes insipidus, is provided.

Amine assisted enzymatic esterification of 1,2-diol monotosylates

The enzymatic esterification of 1,2-diol monotosylates in organic solvent under standard conditions often fails to achieve the desired 50% conversion due to enzyme inactivation by acidic contaminants. The inclusion of an amine affords rapid conversion to

Enzymes in Organic Synthesis: Synthesis of Highly Enantiomerically Pure 1,2-Epoxy Aldehydes, Epoxy Alcohols, Thiirane, Aziridine, and Glyceraldehyde 3-Phosphate

This paper describes a chemoenzymatic procedure for the synthesis of (R)- and (S)-glycidaldehyde diethyl acetal (4 and 5). 2-Acetoxy-3-chloropropanal diethyl acetal (1c) was enantioselectively hydrolyzed by LP-80 lipase to give (S)-3-chloro-2-hydroxypropanal diethyl acetal (2c) and the unreacted acetate (3c), both in >95percent calculated yield and >98percent ee.Both products were subsequently converted to epoxides 4 and 5, respectively.Resolutions of 2-acetoxy-1-(benzyloxy)-3-chloropropane (11a) and 3-(allyloxy)-2-acetoxypropyl p-toluenesulfonate (14b) were similarly carried out to give the corresponding optically active 2-hydroxy and 2-acetoxy derivatives in 90percent and >95percent ee.These products were subsequently converted to the corresponding 1,2-epoxides.Nucleophilic opening of epoxide 4 was exemplified by the syntheses of (R)-3-azido-2-hydroxypropanal and D-glyceraldehyde 3-phosphate.Conversion of the chiral epoxides to thiirane and aziridine was also described.