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

Base Information

• Chemical Name: (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE ACETONIDE
• CAS No.: 150767-96-7
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.203
• Mol file: 150767-96-7.mol

Synonyms:1,3-Benzodioxole-4-carbonitrile,3a,7a-dihydro-2,2-dimethyl-, (3aR-cis)-

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

Chemical Property:

• Boiling Point: 294.6±40.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 1.52628

Purity/Quality:

99%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 3 articles about (+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE ACETONIDE 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: 94.0%

(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile (138769-96-7) + 2,2-dimethoxy-propane (77-76-9) → (1R,6S)-2-cyano-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>nona-2,4-diene (150767-96-7)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1016/0957-4166(96)00064-X

Reference yield:

benzonitrile (100-47-0) → (1R,6S)-2-cyano-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>nona-2,4-diene (150767-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene dioxygenase from Pseudomonas putida F₁

2: 94 percent / toluene-4-sulfonic acid / dimethylformamide / 20 h / Ambient temperature

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0957-4166(96)00064-X

Reference yield:

benzonitrile (100-47-0) → (1R,6S)-2-cyano-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>nona-2,4-diene (150767-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium hydroxide / paraffin oil / pH 6.8 / Microbiological reaction

2: toluene-4-sulfonic acid / acetone / 0 - 20 °C

With ammonium hydroxide; toluene-4-sulfonic acid; In acetone; paraffin oil;

DOI:10.1016/j.tetasy.2015.10.015

upstream raw materials:

(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile

2,2-dimethoxy-propane

benzonitrile

Refernces

• 1、 Tran, Chuong Hao,Crout, David H.G.,Errington, William,Whited, Gregory M.. "Synthesis of (-)-6-hydroxyshikimic acid from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile". . p. 691 - 698. Retrieved 2007/10/03.
• 2、 Blacker, A. John,Booth, R. John,Davies, Gareth M.,Sutherland, James K.. "Syntheses of 6β-hydroxyshikimic acid and its derivatives". . p. 2861 - 2870. Retrieved 2007/10/02.