2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester
CAS No.:184291-71-2
Molecular Formula:C₃₄H₅₈O₅Si
Molecular Weight:574.917
Hs Code.:

2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

Synonyms:2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

There total 9 articles about 2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl 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: 38.0%

: 2,2-Dimethyl-propionic acid (E)-6-benzo[1,3,2]dioxaborol-2-yl-hex-5-enyl ester

: 184292-12-4
tert-Butyl-[(Z)-(2R,3S,4S)-6-iodo-3-(4-methoxy-benzyloxy)-1,2,4-trimethyl-hex-5-enyloxy]-dimethyl-silane

: 184291-71-2
2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; In tetrahydrofuran; for 0.5h; Heating;
DOI:10.1021/ja961374o

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 184291-71-2
2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / NaH

2: 1.) O₃, 2.) Me₂S

4: lutidine

5: 83 percent / HF*pyridine / tetrahydrofuran / 6 h / Ambient temperature

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

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

8: 38 percent / 10percent aq. TlOH, Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; dimethylsulfide; lutidine; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja961374o

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 184291-71-2
2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-12-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-trideca-5,7-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

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

2: 90 percent / NaH

3: 1.) O₃, 2.) Me₂S

5: lutidine

6: 83 percent / HF*pyridine / tetrahydrofuran / 6 h / Ambient temperature

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

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

9: 38 percent / 10percent aq. TlOH, Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; dimethylsulfide; lutidine; hydrogen bromide; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja961374o