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

Base Information

• Chemical Name: (1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one
• CAS No.: 350715-39-8
• Molecular Formula: C₂₇H₃₈O₆
• Molecular Weight: 458.595

Synonyms:(1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

Chemical Property of (1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

There total 13 articles about (1S,4R,8S,9S,10R,11R,12S)-1,8,10-Trihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-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: 89.0%

(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) → (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)

Guidance literature:

With potassium tert-butylate; In benzene; at 20 ℃; for 0.5h;

DOI:10.1021/jo020627v

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-[(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)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / aq. sodium hydroxide / methanol; tetrahydrofuran

2: 89 percent / potassium tert-butoxide / benzene / 0.5 h / 20 °C

With sodium hydroxide; potassium tert-butylate; In tetrahydrofuran; methanol; benzene;

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

(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

4-bromopent-4-en-1-ol

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

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

C₂₇H₃₆O₆

(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

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