141942-84-9

Basic information

• Product Name: BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)-
• Synonyms: (R)-4-CYANO-3-HYDROXY-BUTYRIC ACID METHYL ESTER;BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)-;Methyl (3R)-4-cyano-3-hydroxybutanoate
• CAS NO: 141942-84-9
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.141
• Mol File: 141942-84-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)-(141942-84-9)
• EPA Substance Registry System: BUTANOIC ACID, 4-CYANO-3-HYDROXY-, METHYL ESTER, (3R)-(141942-84-9)

Safety Data

• Hazardous Substances Data: 141942-84-9(Hazardous Substances Data)

Upstream product

• 4509-09-5 Methyl (+/-)-3,4-epoxybutanoate 
• 143-33-9 sodium cyanide 
• 773837-37-9 sodium cyanide 
• 940-47-6 1-chloro-3-phenoxyacetone 

Downstream Products

• 125971-94-0 2-((4R, 6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid tert-butyl ester 
• 125971-93-9 (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate 
• 125988-01-4 tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate 

Relevant articles and documents

Sequential kinetic resolution catalyzed by halohydrin dehalogenase

(Chemical Equation Presented) A sequential kinetic resolution catalyzed by halohydrin dehalogenase was employed for the synthesis of two valuable enantiopure building blocks. Resolution of methyl 4-chloro-3-hydroxybutanoate methylester ((R,S)-2) with use of a Trp249Phe mutant of halohydrin dehalogenase yielded methyl 4-cyano-3-hydroxybutanoate methylester ((S)-4) with 96.8% ee (40% yield) and (S)-2 with 95.2% ee (41% yield). This reaction is carried out in aqueous solution under mild conditions and provides access to a useful statin side-chain building block.

Biocatalytic cascade for the synthesis of enantiopure β-azidoalcohols and β-hydroxynitriles

A three-step, two-enzyme, one-pot reaction sequence starting from prochiral a-chloroketones leading to enantiopure (3- azidoalcohols and (3-hydroxynitriles is described. Asymmetric bioreduction of a-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide and nucleophilic ring opening with azide, N3-, or cyanide, CN-, both catalysed by a nonselective halohydrin dehalogenase (Hhe) proceeded with full retention of configuration to give enantiopure (-azidoalcohols and (3-hydroxynitriles, respectively. Both enantiomers of various optically pure (-azidoalcohols and (-hydroxynitriles were synthesised.