(1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

Base Information

• Chemical Name: (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one
• CAS No.: 350715-38-7
• Molecular Formula: C₂₇H₃₈O₆
• Molecular Weight: 458.595

Synonyms:(1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

Chemical Property of (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

There total 11 articles about (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one 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: 68.0%

4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.01,5]tetradec-7-yl]-pent-4-enal (350715-36-5) → (1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecan-2-one (350715-39-8) + (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadecan-3-one (350715-38-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1021/jo020627v

Reference yield:

4-bromopent-4-en-1-ol (64180-78-5) → (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadecan-3-one (350715-38-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 15.74 g / Et₃N; DBU / CH₂Cl₂

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

3.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

3.2: 88 percent / tetrahydrofuran / -78 - -30 °C

4.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

4.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

5.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 1.48 h / -78 - -40 °C

5.2: 81 percent / tetrahydrofuran; toluene / 3 h / -78 °C

6.1: 54 percent / NMO*H₂O; osmium tetraoxide; water / acetone / 120 h / 0 °C

7.1: pyridine / CH₂Cl₂; toluene / 0.25 h / -78 °C

8.1: 890 mg / methanol; Dowex 50X₄-400 / 2.5 h

9.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.33 h / -78 - 20 °C

10.1: 68 percent / aq. sodium hydroxide / methanol; tetrahydrofuran

With pyridine; methanol; sodium hydroxide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; Dowex 50X₄-400; water; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane; 3.2: Wittig condensation / 9.1: Swern oxidation;

DOI:10.1021/jo020627v

Reference yield:

((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane (120001-35-6) → (1S,2R,4S,5S,9R,11S,12S)-5,11,12-Trihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadecan-3-one (350715-38-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

1.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

2.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

2.2: 88 percent / tetrahydrofuran / -78 - -30 °C

3.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

3.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

4.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 1.48 h / -78 - -40 °C

4.2: 81 percent / tetrahydrofuran; toluene / 3 h / -78 °C

5.1: 54 percent / NMO*H₂O; osmium tetraoxide; water / acetone / 120 h / 0 °C

6.1: pyridine / CH₂Cl₂; toluene / 0.25 h / -78 °C

7.1: 890 mg / methanol; Dowex 50X₄-400 / 2.5 h

8.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.33 h / -78 - 20 °C

9.1: 68 percent / aq. sodium hydroxide / methanol; tetrahydrofuran

With pyridine; methanol; sodium hydroxide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; Dowex 50X₄-400; water; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane; 2.2: Wittig condensation / 8.1: Swern oxidation;

DOI:10.1021/jo020627v

upstream raw materials:

4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal

4-bromopent-4-en-1-ol

((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane

4-bromo-4-pentenoic acid tert-butyl ester

Downstream raw materials:

(1S,4R,8S,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

(1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

C₄₁H₄₄O₉

C₃₅H₄₄O₈

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