7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane

Base Information

• Chemical Name: 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane
• CAS No.: 133732-39-5
• Molecular Formula: C₂₈H₂₈O₈
• Molecular Weight: 492.526
• Mol file: 133732-39-5.mol

Synonyms:7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane

Chemical Property of 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane

There total 23 articles about 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane 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: 97.0%

2-(4-acetoxy-3-methoxyphenyl)acetic acid (5447-38-1) + 1-benzyl-7-(3-hydroxyprop-1-ynyl)-2,9,10-trioxatricyclo<4.3.1.03,8>decane (133707-30-9) → 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.03,8>decane (133732-39-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1039/P19920001229

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.03,8>decane (133732-39-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) O₂, 2) thiourea / 1) 5,10,15,20-tetraphenyl-21H,23H-porphine / 1) CH₂Cl₂, -10 deg C, 5.5 h, 2) MeOH, room temperature, overnight

2: 72 percent / NEt₃ / dimethylformamide / 24 h / 0 deg C to room temperature

3: 92 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 96 h / Ambient temperature

4: 1) butyllithium, diethylaluminium chloride / 1) toluene, hexane, -40 deg C, 30 min, 2) 3.5 h, -40 deg C

5: 66 percent / pyridine / 1.33 h / 0 °C

6: 82 percent / citric acid monohydrate / methanol / 4.33 h / 18 °C

7: 76 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

8: 83 percent / citric acid monohydrate / methanol; H₂O / 0.67 h / Heating

9: 73 percent / 2,4,6-trimethylpyridine, powdered 4 Angstroem molecular sieve / 10 h / Heating

10: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / Ambient temperature

11: 97 percent / dicyclohexylcarbodiimide, 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; dmap; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; oxygen; diethylaluminium chloride; sodium hydrogencarbonate; triethylamine; thiourea; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; citric acid; 5,15,10,20-tetraphenylporphyrin; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/P19920001229

Reference yield:

phenylacetic acid (103-82-2) → 7-<3-(4-acetoxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-1-benzyl-2,9,10-trioxatricyclo<4.3.1.03,8>decane (133732-39-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

2: 83 percent / citric acid monohydrate / methanol; H₂O / 0.67 h / Heating

3: 73 percent / 2,4,6-trimethylpyridine, powdered 4 Angstroem molecular sieve / 10 h / Heating

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / Ambient temperature

5: 97 percent / dicyclohexylcarbodiimide, 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; citric acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1039/P19920001229

upstream raw materials:

2-(4-acetoxy-3-methoxyphenyl)acetic acid

3-((3S,6R,7R,8R)-1-Benzyl-2,9,10-trioxa-tricyclo[4.3.1.0^3,8]dec-7-yl)-prop-2-yn-1-ol

phenylacetic acid

(1S,4R)-Cyclohex-2-ene-1,4-diol

Downstream raw materials:

(4-Hydroxy-3-methoxy-phenyl)-acetic acid 3-((3S,6R,7R,8R)-1-benzyl-2,9,10-trioxa-tricyclo[4.3.1.0^3,8]dec-7-yl)-prop-2-ynyl ester

1-benzyl-7-<3-(4-hydroxy-3-methoxyphenyl)acetoxyprop-1-ynyl>-2,9,10-trioxatricyclo<4.3.1.0^3,8>decane