(1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate

Base Information

• Chemical Name: (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate
• CAS No.: 321146-17-2
• Molecular Formula: C₃₅H₄₂O₁₂
• Molecular Weight: 654.711

Synonyms:(1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate

Chemical Property of (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate

Chemical Property:

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Technology Process of (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate

There total 7 articles about (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate 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: 72.0%

4,4'-Methylene-di[(1R,1'S,6R,6'S)-6-acetoxycyclohept-3-en-1-yl] bis(4-methoxybenzoate) (321146-15-0) → (1S*,6S*)-6-Acetoxy-4-{(1R*,2S*,4R*,6R*)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}metylcyclohept-3-en-1-yl 4-methoxybenzoate + (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate (321146-17-2)

Guidance literature:

With methanesulfonamide; AD-mix-β; water; In acetonitrile; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W

Reference yield:

2,2'-difurylmethane (1197-40-6) → (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate (321146-17-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Et₃N; CF₃CHOHCF₃ / 20 °C

1.2: 55 percent / NH₄Cl; Zn/Cu / methanol / 120 h / 20 °C

2.1: 98 percent / K-selectride / tetrahydrofuran / 15 h / -78 - 20 °C

3.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

4.1: 96 percent / BCl₃ / CH₂Cl₂ / 4 h / -10 °C

5.1: 17.6 g / pyridine; DMAP / 15 h / 20 °C

6.1: Bu₃SnH; AIBN / toluene / 4 h / 85 °C

6.2: 84 percent / KF / diethyl ether / 4 h / 20 °C

7.1: 72 percent / AD-mix-β; H2O; MeSO2NH2 / 2-methyl-propan-2-ol; acetonitrile / 24 h / 0 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); methanesulfonamide; 1,1,1,3',3',3'-hexafluoro-propanol; AD-mix-β; water; tri-n-butyl-tin hydride; boron trichloride; potassium tri-sec-butyl-borohydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W

Reference yield:

meso-1,1'-methylenedi[(1R,1'S,5S,5'R)-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl] (321146-05-8) → (1R,6R)-6-Acetoxy-4-{(1R,2S,4S,6R)-6-acetoxy-1,2-dihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate (321146-17-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / K-selectride / tetrahydrofuran / 15 h / -78 - 20 °C

2.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 96 percent / BCl₃ / CH₂Cl₂ / 4 h / -10 °C

4.1: 17.6 g / pyridine; DMAP / 15 h / 20 °C

5.1: Bu₃SnH; AIBN / toluene / 4 h / 85 °C

5.2: 84 percent / KF / diethyl ether / 4 h / 20 °C

6.1: 72 percent / AD-mix-β; H2O; MeSO2NH2 / 2-methyl-propan-2-ol; acetonitrile / 24 h / 0 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); methanesulfonamide; AD-mix-β; water; tri-n-butyl-tin hydride; boron trichloride; potassium tri-sec-butyl-borohydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W

upstream raw materials:

4,4'-Methylene-di[(1R,1'S,6R,6'S)-6-acetoxycyclohept-3-en-1-yl] bis(4-methoxybenzoate)

2,2'-difurylmethane

meso-1,1'-methylenedi[(1R,1'S,5S,5'R)-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-1-yl]

meso-1,1'-methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]

Downstream raw materials:

(1R,6R)-6-Hydroxy-4-{(1R,2S,4S,6S)-1,2,3-trihydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1'-yl}methylcyclohept-3-en-1-yl 4-methoxybenzoate

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