(-)-2,3-dihydroxy-3-phenylpropanenitrile

Base Information

• Chemical Name: (-)-2,3-dihydroxy-3-phenylpropanenitrile
• CAS No.: 133520-54-4
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.176
• Mol file: 133520-54-4.mol

Synonyms:(-)-2,3-dihydroxy-3-phenylpropanenitrile

Chemical Property of (-)-2,3-dihydroxy-3-phenylpropanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-2,3-dihydroxy-3-phenylpropanenitrile

There total 13 articles about (-)-2,3-dihydroxy-3-phenylpropanenitrile 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: 99.0%

cinnamic nitrile (1885-38-7) → (2SR,3RS)-2,3-dihydroxy-3-phenylpropanenitrile (79224-27-4,79224-28-5,82082-56-2,133520-53-3,133520-54-4)

Guidance literature:

With 4-methylmorpholine N-oxide; citric acid; potassium dioxotetrahydroxoosmate(VI); In water; tert-butyl alcohol; at 20 ℃; for 3h;

DOI:10.1002/1615-4169(200206)344:3/4<421::AID-ADSC421>3.0.CO;2-F

Reference yield: 45.0%

(±)-trans-phenyloxiriane-2-carbonitrile (33863-75-1,33984-95-1,33984-96-2) → trans-3-phenyloxirane-2-carbonitrile + (-)-2,3-dihydroxy-3-phenylpropanenitrile (133520-54-4)

Guidance literature:

With Epoxide hydrolase Kau₂ from Escherichia coli RE₃; In aq. phosphate buffer; tert-butyl methyl ether; at 27 ℃; pH=7; enantioselective reaction; Resolution of racemate;

DOI:10.1002/adsc.201401164

Reference yield: 39.0%

(±)-cis-phenyloxirane-2-carbonitrile (33863-75-1,33984-95-1,33984-96-2) → (2SR,3RS)-2,3-dihydroxy-3-phenylpropanenitrile (79224-27-4,79224-28-5,82082-56-2,133520-53-3,133520-54-4)

Guidance literature:

With whole cells of Mortrierella isabellina DSM 1414; In ethanol; at 50 ℃; for 5.5h;

DOI:10.1016/j.tetasy.2008.06.004

upstream raw materials:

3-(Dimethylthexylsiloxy)-2-hydroxy-3-phenylpropannitril

vinyl acetate

2,3-dihydroxy-3-phenylpropanenitrile

(±)-trans-phenyloxiriane-2-carbonitrile

Downstream raw materials:

methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate

2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonitril

Refernces

• 1、 Zagozda, Malgorzata,Plenkiewicz, Jan. "Biotransformations of 2,3-epoxy-3-arylpropanenitriles by Debaryomyces hansenii and Mortierella isabellina cells". . p. 1454 - 1459. Retrieved 2008/12/20.
• 2、 Dupau, Philippe,Epple, Robert,Thomas, Allen A.,Fokin, Valery V.,Sharpless, K. Barry. "Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media: Old Process, New Tricks". . p. 421 - 433. Retrieved 2007/10/03.