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

Base Information

Chemical Name:1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene
CAS No.:835929-81-2
Molecular Formula:C₆₀H₈₈O₅Si₂
Molecular Weight:945.527
Hs Code.:

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

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

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

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

There total 6 articles about 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-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:

: 835929-80-1
(Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-enal

: 2741-38-0
allyldiphenylphosphine

: 835929-81-2
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene

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

Guidance literature:: allyldiphenylphosphine; With titanium(IV) isopropylate; tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

(Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-enal; In tetrahydrofuran; pentane; at -78 - 0 ℃;

With methyl iodide; In tetrahydrofuran; pentane; at 20 ℃; for 16h; Title compound not separated from byproducts;
DOI:10.1021/ol047686a

Reference yield:

: tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane

: 835929-81-2
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene

Guidance literature:: Multi-step reaction with 5 steps

1.1: ZnCl₂; t-BuLi / diethyl ether / -78 - 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether

2.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

3.1: 87 percent / DMAP; pyridine / 18 h / Heating

4.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

5.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / 0.5 h / -78 °C

5.2: tetrahydrofuran; pentane / -78 - 0 °C

5.3: MeI / tetrahydrofuran; pentane / 16 h / 20 °C

With pyridine; titanium(IV) isopropylate; dmap; water; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/ol047686a

Reference yield:

: 835929-77-6
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

: 835929-81-2
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / DMAP; pyridine / 18 h / Heating

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

3.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / -78 - 0 °C

3.3: MeI / tetrahydrofuran; pentane / 16 h / 20 °C

With pyridine; titanium(IV) isopropylate; dmap; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/ol047686a