(1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane

Base Information

• Chemical Name: (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane
• CAS No.: 860401-63-4
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 860401-63-4.mol

Synonyms:(1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane

Chemical Property of (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane

There total 2 articles about (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane 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: 100.0%

(1S,2E,4S,5R)-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexan-1-ol (860401-62-3) + benzoyl chloride (98-88-4) → (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane (860401-63-4)

Guidance literature:

With dmap; In dichloromethane; at 24 ℃; for 2h;

DOI:10.1055/s-2005-865291

Reference yield:

(2E,4S,5R)-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexan-1-one (860401-61-2) → (1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane (860401-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.83 h / -78 °C

2: 100 percent / DMAP / CH₂Cl₂ / 2 h / 24 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane;

DOI:10.1055/s-2005-865291

Reference yield:

(1S,2E,4S,5R)-1-benzoyloxy-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexane (860401-63-4) → (1S,2S,4R,5S)-2-benzoyloxy-1-vinyl-7-oxabicyclo[2.2.1]heptan-5-ol (860401-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / aq. AcOH / tetrahydrofuran / 9.5 h / 25 °C

2: 96 percent / I(collidine)2PF₆ / acetonitrile / 4 h / 20 °C

3: 96 percent / DBU / toluene / 18 h / 105 °C

With acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1055/s-2005-865291

upstream raw materials:

(1S,2E,4S,5R)-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexan-1-ol

benzoyl chloride

(2E,4S,5R)-2-ethylidene-4,5-(dimethylmethylenedioxy)cyclohexan-1-one

Downstream raw materials:

(1S,2S,4R,5S)-2-benzoyloxy-1-vinyl-7-oxabicyclo[2.2.1]heptan-5-ol

(1R,2S,4R,5S)-2-benzoyloxy-1-[(1'S)-1'-iodoethyl]-7-oxabicyclo[2.2.1]heptan-5-ol

(1S,2S,4R,5S)-2-benzoyloxy-5-(tert-butyldiphenylsilyloxy)-1-vinyl-7-oxabicyclo[2.2.1]heptane