(+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE

Base Information

• Chemical Name: (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE
• CAS No.: 138769-96-7
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Mol file: 138769-96-7.mol

Synonyms:CIS-(1S,2R)-3-CYANO-3,5-CYCLOHEXADIENE-1,2- DIOL;(+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE

Chemical Property of (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE

Chemical Property:

• Boiling Point: 341.2±42.0 °C(Predicted)
• PKA: 12.20±0.60(Predicted)
• PSA: 64.25000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: -0.27202

Purity/Quality:

98%min ^*data from raw suppliers

(+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE is a chiral cis-dihydrodiol metabolite derived from the enzymatic cis-dihydroxylation of benzonitrile, catalyzed by chlorobenzene dioxygenase (CDO) or toluene dioxygenase (TDO). It exhibits high regio- and stereoselectivity, with enantiomeric excess ranging from 42.9% to 97.1%, and serves as a valuable intermediate in organic synthesis, such as in the preparation of (-)-6-hydroxyshikimic acid. (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE can also be formed indirectly via the oxidation of benzyl azide to benzonitrile, followed by TDO-catalyzed dihydroxylation. Its production is limited by toxicity but can be enhanced through optimized biocatalytic systems.

Technology Process of (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE

There total 7 articles about (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE 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: 52.0%

tri-n-butyltin cyanide (2179-92-2) + cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene (138769-92-3) → (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile (138769-96-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 50 ℃; for 4h;

DOI:10.1039/c39910001630

Reference yield:

benzonitrile (100-47-0) → (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile (138769-96-7)

Guidance literature:

In ethanol; at 28 ℃; aq. culture of Pseudomonas putida UV₄, pH ca. 7.5, 20percent aq. KOH;

Reference yield:

benzyl azide (622-79-7) → (1S,2R)-3-azidomethyl-cyclohex-3,5-diene-1,2-diol + (1S,2R,6R)-6-azido-3-methylenecyclohex-4-ene-1,2-diol + (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile (138769-96-7)

Guidance literature:

With 2,3,4,5,6-pentahydroxy-hexanal; ampicillin sodium salt; In aq. phosphate buffer; paraffin oil; at 37 ℃; pH=6.8; Overall yield = 30 %; stereoselective reaction; Microbiological reaction; Enzymatic reaction;

DOI:10.1021/ol503708v

upstream raw materials:

tri-n-butyltin cyanide

cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene

benzonitrile

iodobenzene

Downstream raw materials:

(1R,6S)-2-cyano-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>nona-2,4-diene

m-cyanophenol

(3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-1-cyclohexene-1-carbonitrile

(1S,2R,3S)-3-cyanocyclohexane-1,2-diol