tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

Base Information

Chemical Name:tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane
CAS No.:1445569-58-3
Molecular Formula:C₂₉H₄₉IO₄Si
Molecular Weight:616.696
Hs Code.:

Synonyms:tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

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Chemical Property of tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

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Technology Process of tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

There total 16 articles about tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1445569-56-1
(R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-ol

: 1445569-58-3
tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol401543b

Reference yield:

: 1445569-13-0
5-(tert-butyldiphenylsilyloxy)-3,3-dimethylpentan-2-one

: 1445569-58-3
tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydride / 1,2-dimethoxyethane / 0.17 h / 0 - 20 °C / Inert atmosphere

1.2: 72 h / 120 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

3.1: sodium hydride / 1,2-dimethoxyethane / 0.17 h / 0 °C / Inert atmosphere

3.2: 21 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / Inert atmosphere

5.2: 4 h / -78 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

6.2: 4 h / -78 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

7.2: -78 - 20 °C / Inert atmosphere

8.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -60 °C / Inert atmosphere

8.2: -60 - 20 °C / Inert atmosphere

9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; diethyl ether / 0 - 20 °C / Inert atmosphere

9.2: 2 h / -78 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; toluene; 1.2: |Horner-Wadsworth-Emmons Olefination / 5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 7.1: |Swern Oxidation;
DOI:10.1021/ol401543b

Reference yield:

: 1445569-19-6
(2E)-6-(tert-butyl-diphenyl-silanyloxy)-3,4,4-trimethyl-hex-2-enoic acid ethyl ester

: 1445569-58-3
tert-butyl((R,1Z,6E)-1-iodo-1-(4-isopropyl-2,3-dimethoxyphenyl)-8-methoxy-5,5,6-trimethylocta-1,6-dien-3-yloxy)dimethylsilane

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

2.1: sodium hydride / 1,2-dimethoxyethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 21 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / Inert atmosphere

4.2: 4 h / -78 - 20 °C / Inert atmosphere

5.1: diethylzinc / hexane; toluene / 4 h / Reflux; Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

5.3: 12 h / 20 °C / Inert atmosphere

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; diethyl ether / 0 - 20 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; diethylzinc; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; toluene; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/ol401543b