Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Base Information

• Chemical Name: Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester
• CAS No.: 90741-87-0
• Molecular Formula: C₂₈H₃₃NO₄
• Molecular Weight: 447.574

Synonyms:Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Chemical Property of Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

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Technology Process of Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

There total 9 articles about Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester 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: 80.0%

Acetic acid (3E,9E)-(1R,11S,14S)-16-benzyl-14-methyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9,12-trien-2-yl ester (90741-86-9) → Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (90741-87-0)

Guidance literature:

With borontrifluoride acetic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ja00328a053

Reference yield:

C32H45NO5SSi (90741-85-8) → Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (90741-87-0) + Acetic acid (3E,9E)-(1R,2R,11S,14S)-16-benzyl-13,14-dimethyl-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9,12-trien-2-yl ester (90741-88-1)

Guidance literature:

With cesium fluoride; In dimethyl sulfoxide; at 20 ℃; for 1.5h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00328a053

Reference yield:

C31H41NO4SSi → Acetic acid (3E,9E)-(1R,2R,11R,14S)-16-benzyl-14-methyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (90741-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) Zn / 1.) DME; 2.) CH₃CO₂H

2: 90 percent / MCPBA

3: CsF / dimethylsulfoxide / 1.5 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; cesium fluoride; zinc; In dimethyl sulfoxide;

DOI:10.1021/ja00328a053

upstream raw materials:

Acetic acid (3E,9E)-(1R,11S,14S)-16-benzyl-14-methyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9,12-trien-2-yl ester

C₃₂H₄₅NO₅SSi

Acetic acid (E)-(1R,11S,14S)-16-benzyl-14-methyl-3-methylsulfanyl-6,18-dioxo-13-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Acetic acid [(3aR,4S,7S)-1-benzyl-4-((E)-3-chloro-propenyl)-7-methyl-3-oxo-6-trimethylsilanylmethyl-1,2,3,4,7,7a-hexahydro-isoindol-3a-yl]-(5-oxo-tetrahydro-thiopyran-2-yl)-methyl ester

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