(R)-(-)-methyl-(3-O--4-cyano)-butanoate

Base Information

• Chemical Name: (R)-(-)-methyl-(3-O--4-cyano)-butanoate
• CAS No.: 147963-52-8
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Mol file: 147963-52-8.mol

Synonyms:

Chemical Property of (R)-(-)-methyl-(3-O--4-cyano)-butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-methyl-(3-O--4-cyano)-butanoate

There total 6 articles about (R)-(-)-methyl-(3-O--4-cyano)-butanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

3-O-(benzyl)-glutaronitrile (138145-57-0) → (S)-(+)-3-O-(benzyl)-4-cyanobutanoic acid (138145-60-5) + (R)-(-)-methyl-(3-O--4-cyano)-butanoate (138145-60-5,147963-52-8)

Guidance literature:

at 30 ℃; for 48h; Title compound not separated from byproducts; Rhodococcus sp. (SP 361), pH 7;

DOI:10.1016/S0957-4166(00)80215-3

Reference yield: 52.0%

(S)-(-)-methyl-(3-O--4-bromo)-butanoate → (R)-(-)-methyl-(3-O--4-cyano)-butanoate (138145-60-5,147963-52-8)

Guidance literature:

With sodium cyanide; In dimethyl sulfoxide; for 4h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80215-3

Reference yield:

3-hydroxyglutaronitrile (13880-89-2) → (R)-(-)-methyl-(3-O--4-cyano)-butanoate (138145-60-5,147963-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / NaH / tetrahydrofuran

2: water, Brevibacterium R₃₁₂ cells / 24 h / 30 °C

With Brevibacterium R₃₁₂ cells; water; sodium hydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)01259-2

upstream raw materials:

3-O-(benzyl)-glutaronitrile

3-hydroxyglutaronitrile

benzyl bromide

O-benzyl 2,2,2-trichloroacetimidate