(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Base Information

• Chemical Name: (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene
• CAS No.: 86782-19-6
• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.337
• Mol file: 86782-19-6.mol

Synonyms:(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Chemical Property of (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

There total 22 articles about (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 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: 69.0%

DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol (74766-84-0,96291-87-1) → trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene (74766-85-1,86782-19-6)

Guidance literature:

With zinc; In ethanol; at 70 ℃; for 0.05h;

DOI:10.1246/cl.1980.379

Reference yield:

benzoyl chloride (98-88-4) → (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (86782-19-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 - 25 °C

2: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

4: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

5: 89 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 2.5 h / 0 °C

6: 80 percent / TFA / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

7: 1.) 1,1'-thiocarbonyldiimidazole, 2.) P(OMe)3 / 1.) TolH, reflux, 24 h, 2.) reflux, 24 h

8: 80 percent / aq. HF / acetonitrile / 6 h / Ambient temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; hydrogen fluoride; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo970907o

Reference yield:

sodium benzoate (532-32-1) → trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene (74766-85-1,86782-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / H₂O; dimethylformamide / 24 h / Ambient temperature

2: 62 percent / zinc / ethanol / 0.33 h / 70 °C

With zinc; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.56.1710

upstream raw materials:

(1S)-(1,4/2,3)-3,4-diacetoxy-5-<(benzoyloxy)methyl>-1,2-dibromocyclohex-5-ene

(2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

(1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

Downstream raw materials:

(2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

(2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

DL-3,4-di-O-acetyl-1,2-anhydro-(1,2/3,4)-2C-(benzoyloxymethyl)-5-cyclohexene-1,2,3,4-tetrol

D,L-(1,2,4/3)-3,4-di-O-acetyl-1,2-anhydro-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4,-tetrol