(S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol

Base Information

• Chemical Name: (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol
• CAS No.: 196605-90-0
• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.371
• Mol file: 196605-90-0.mol

Synonyms:(S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol

Chemical Property of (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(1S,2S)-1,2-Bis(3,5-dimethylphenyl)ethane-1,2-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol

There total 6 articles about (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol 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: 59.0%

(E)-1,2-bis(3,5-dimethylphenyl)ethene (13863-27-9) → (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol (196605-90-0)

Guidance literature:

(E)-1,2-bis(3,5-dimethylphenyl)ethene; With 4-hydroxyphenyl 4-chlorobenzoate; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); In water; tert-butyl alcohol; at 20 ℃; for 48h;

With sodium sulfite; In water; tert-butyl alcohol; for 0.5h;

DOI:10.1002/adsc.200404168

Reference yield:

(E)-1,2-bis(3,5-dimethylphenyl)ethene (13863-27-9) → (R,R)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol (158391-63-0) + (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol (196605-90-0)

Guidance literature:

With potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; In water; tert-butyl alcohol; at 0 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1002/anie.200504432

Reference yield:

3,5-dimethylbenzaldehyde (5779-95-3) → (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol (196605-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / TiCl₄; Zn / tetrahydrofuran / Heating

2: K₃Fe(CN)6; K₂CO₃; (DHDQ)2PHAL / K₂OsO₂(OH)4; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

With titanium tetrachloride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); zinc; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; In tetrahydrofuran; water; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;

DOI:10.1002/anie.200504432

upstream raw materials:

1,2-bis(3,5-dimethylphenyl)ethane-1,2-dione

(E)-1,2-bis(3,5-dimethylphenyl)ethene

3,5-dimethylbenzaldehyde

1-bromomethyl-3,5-dimethylbenzene

Downstream raw materials:

(1R,2R)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diamine

(R,R)-1,2-diazido-1,2-bis(3,5-dimethylphenyl)ethane

(1R,2R)-1,2-N,N'-bis(p-toluenesulfonylamino)-1,2-bis(3,5-dimethylphenyl)ethane