(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

Base Information

Chemical Name:(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione
CAS No.:201355-10-4
Molecular Formula:C₃₅H₅₈O₆Si
Molecular Weight:602.927
Hs Code.:

Synonyms:(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

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Chemical Property of (2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

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Technology Process of (2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

There total 17 articles about (2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione 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: 85.0%

: 201355-15-9
(2E)-(4R,8S,10R,12S)-4-p-methoxybenzyloxy-8-hydroxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6-one

: 201355-10-4
(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4039(97)10483-X

Reference yield:

: 862474-98-4
(5E)-(4R)-4-p-methoxybenzyloxy-hepta-1,5-diene

: 201355-10-4
(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 1.01 g / aq. CuCl; O₂ / PdCl₂ / dimethylformamide / 14 h / 20 °C

2: Et₃N / diethyl ether / 0.5 h / 0 °C

3: diethyl ether / 16 h / -78 - -20 °C

With oxygen; triethylamine; copper(l) chloride; palladium dichloride; In diethyl ether; N,N-dimethyl-formamide; 1: Wacker oxidation;
DOI:10.1039/b504148a

Reference yield:

: 24581-03-1
(5E)-hepta-1,5-dien-4-ol

: 201355-10-4
(2E)-(4R,10S,12S)-4-p-methoxybenzyloxy-10-methoxy-12-(triisopropylsilyloxy)-14-ethyl-pentadeca-2,14-dien-6,8-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 40 percent / diisopropyl L-tartrate; 4 Angstroem molecular sieves; tert-butyl hydroperoxide / Ti(Oi-Pr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -20 °C

2: 69 percent / KH; tetrabutylammonium iodide / tetrahydrofuran / 14 h / 20 °C

3: 1.01 g / aq. CuCl; O₂ / PdCl₂ / dimethylformamide / 14 h / 20 °C

4: Et₃N / diethyl ether / 0.5 h / 0 °C

5: diethyl ether / 16 h / -78 - -20 °C

With tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; oxygen; tetra-(n-butyl)ammonium iodide; potassium hydride; triethylamine; copper(l) chloride; titanium(IV) isopropylate; palladium dichloride; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Sharpless asymmetric epoxidation / 3: Wacker oxidation;
DOI:10.1039/b504148a