(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

Base Information

• Chemical Name: (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
• CAS No.: 350715-47-8
• Molecular Formula: C₃₃H₅₂O₆Si
• Molecular Weight: 572.858

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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:

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,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecan-2-one (350715-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: KOMe / methanol / 20 °C

With potassium methanolate; In methanol;

DOI:10.1021/ol0100733

Reference yield:

(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,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecan-2-one (350715-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / KOtBu / benzene / 0.5 h / 20 °C

With potassium tert-butylate; In benzene;

DOI:10.1021/ol0100733

Reference yield:

(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,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[10.2.1.04,9]pentadecan-2-one (350715-47-8)

Guidance literature:

DOI:10.1021/ol0100733

upstream raw materials:

(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

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

Downstream raw materials:

C₃₃H₅₀O₆Si

C₄₀H₅₄O₈Si

Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,11-dihydroxy-2-methanesulfonyloxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

C₃₅H₅₂O₈Si

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