(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

Base Information

Chemical Name:(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one
CAS No.:184291-84-7
Molecular Formula:C₃₀H₅₀O₄Si
Molecular Weight:502.81
Hs Code.:

Synonyms:(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

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Chemical Property of (Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

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Technology Process of (Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

There total 9 articles about (Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-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:

: 184292-25-9
(Z)-(8S,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-ol

: 184291-84-7
(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 0.5h; Yield given; Ambient temperature;
DOI:10.1021/ja961374o

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 184291-84-7
(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / NaH / dimethylformamide; tetrahydrofuran / 48 h / Ambient temperature

2: 1.) O₃, Sudan III, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 2 h

3: 1.) NaHMDS, 2.) HMPA / 1.) THF, RT, 20 min, 2.) THF, RT, 1 h

4: 80 percent / Pd(PPh₃)4 / tetrahydrofuran / 24 h / Ambient temperature

5: 88 percent / aq. TFA / tetrahydrofuran / 8 h / Ambient temperature

6: 456 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 458 mg / tetrahydrofuran / 0.5 h / Ambient temperature

8: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide; oil scarlet; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; ozone; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja961374o

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 184291-84-7
(Z)-(8R,9S,10S)-9-(4-Methoxy-benzyloxy)-8,10-dimethyl-1-triethylsilanyloxy-tetradeca-11,13-dien-7-one

Guidance literature:: Multi-step reaction with 9 steps

1: 48percent aq. HBr / 0.5 h / Ambient temperature

2: 93 percent / NaH / dimethylformamide; tetrahydrofuran / 48 h / Ambient temperature

3: 1.) O₃, Sudan III, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 2 h

4: 1.) NaHMDS, 2.) HMPA / 1.) THF, RT, 20 min, 2.) THF, RT, 1 h

5: 80 percent / Pd(PPh₃)4 / tetrahydrofuran / 24 h / Ambient temperature

6: 88 percent / aq. TFA / tetrahydrofuran / 8 h / Ambient temperature

7: 456 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / Ambient temperature

8: 458 mg / tetrahydrofuran / 0.5 h / Ambient temperature

9: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide; oil scarlet; hydrogen bromide; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; ozone; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja961374o