ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate

Base Information

• Chemical Name: ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate
• CAS No.: 164199-49-9
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.403
• Mol file: 164199-49-9.mol

Synonyms:ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate

Chemical Property of ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate

There total 1 articles about ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate 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: 85.0%

diazodiphenylmethane (908093-98-1) + ethyl (1R,2R)-1,2-bis(hydroxymethyl)-1-cyclopropanecarboxylate (144985-81-9) → ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate (164199-49-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

DOI:10.1021/jm9904194

Reference yield: 90.0%

ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate (164199-49-9) → (1S,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-methanol (164199-50-2)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 72 ℃; for 16h;

DOI:10.1021/jm9904194

Reference yield:

ethyl (1R,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-carboxylate (164199-49-9) → 1-((1S,7R)-4,4-Diphenyl-3,5-dioxa-bicyclo[5.1.0]oct-1-ylmethyl)-5-ethynyl-1H-pyrimidine-2,4-dione

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / LiBH₄ / tetrahydrofuran / 16 h / 72 °C

2: 90 percent / CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

3: K₂CO₃; 18-crown-6 / dimethylformamide / 2 h / 60 °C

With lithium borohydride; 18-crown-6 ether; carbon tetrabromide; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Bromination / 3: Alkylation;

DOI:10.1021/jm9904194

upstream raw materials:

diazodiphenylmethane

ethyl (1R,2R)-1,2-bis(hydroxymethyl)-1-cyclopropanecarboxylate

Downstream raw materials:

(1S,7R)-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane-1-methanol

(1R,7R)-1-bromomethyl-3,5-dioxa-4,4-diphenylbicyclo[5.1.0]octane

1-[(1'S,2'R)-1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl-5-[(E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione

5-((E)-2-Bromo-vinyl)-1-((1S,7R)-4,4-diphenyl-3,5-dioxa-bicyclo[5.1.0]oct-1-ylmethyl)-1H-pyrimidine-2,4-dione