1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

Base Information

Chemical Name:1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene
CAS No.:633293-91-1
Molecular Formula:C₄₄H₈₀O₆Si₂
Molecular Weight:761.287
Hs Code.:

1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

Synonyms:1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

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Chemical Property of 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

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Technology Process of 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

There total 14 articles about 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene 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: 67.0%

: 850211-69-7
tert-Butyl-[(Z)-(1S,2R,3S,4S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octa-5,7-dienyloxy]-dimethyl-silane

: 852049-56-0
tert-Butyl-((Z)-(2S,3R,4S)-6-iodo-3-methoxymethoxy-2,4-dimethyl-hept-5-enyloxy)-dimethyl-silane

: 633293-91-1
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tert.-butyl lithium; caesium carbonate; 9-methoxy-9-BBN;
DOI:10.1002/cjoc.201090240

Reference yield:

: 633293-72-8
C₄₁H₇₆O₇Si₂

: 2741-38-0
allyldiphenylphosphine

: 633293-91-1
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

: C₄₄H₈₀O₆Si₂

Guidance literature:: allyldiphenylphosphine; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃; for 0.583333h;

C₄₁H₇₆O₇Si₂; titanium(IV) isopropylate; In tetrahydrofuran; at -78 ℃; for 0.5h;

With methyl iodide; at 0 - 20 ℃; for 16h;

Reference yield:

: (Z)-(2S,3R,4S)-6-Iodo-3-methoxymethoxy-2,4-dimethyl-hept-5-en-1-ol

: 633293-91-1
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

2.1: t-BuLi; MeO-9-BBN / various solvents / 1 h / 20 °C

2.2: 79 percent / Cs₂CO₃ / Pd(dppf)Cl₂ / various solvents / 20 h / 20 °C

With 1H-imidazole; tert.-butyl lithium; 9-methoxy-9-BBN; In dichloromethane; various solvents; 2.2: Suzuki cross-coupling;
DOI:10.1021/ol050455z