(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

Base Information

Chemical Name:(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane
CAS No.:552289-38-0
Molecular Formula:C₁₉H₃₅IOSi
Molecular Weight:434.476
Hs Code.:

Synonyms:(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

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Chemical Property of (2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

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Technology Process of (2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

There total 6 articles about (2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane 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: 76.0%

: 552289-50-6
trifluoromethanesulfonic acid (3R)-6-methyl-3-[1(S)-methyl-2-(triisopropylsilyloxy)ethyl]cyclohexa-1,5-dienyl ester

: 552289-38-0
(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

Guidance literature:: trifluoromethanesulfonic acid (3R)-6-methyl-3-[1(S)-methyl-2-(triisopropylsilyloxy)ethyl]cyclohexa-1,5-dienyl ester; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; lithium chloride; In tetrahydrofuran; at 23 - 70 ℃; Inert atmosphere;

With N-iodo-succinimide; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo9010156

Reference yield: 65.0%

: (S)-2-Methyl-5-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohex-2-enol

: 552289-38-0
(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

Guidance literature:: (S)-2-Methyl-5-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohex-2-enol; With N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; lithium chloride; In tetrahydrofuran; Heating;

With N-iodo-succinimide; at 0 ℃;
DOI:10.1021/ja035445c

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 552289-38-0
(2S)-{2-[1(R)-3-iodo-4-methylcyclohexa-2,4-dienyl]propoxy}triisopropylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: imidazole / dimethylformamide / 20 °C

2.1: LDA; 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine / tetrahydrofuran / -78 - 20 °C

2.2: (Ph₃P)4Pd; LiCl; (Me₃Sn)2 / tetrahydrofuran / Heating

2.3: 65 percent / N-iodosuccinimide / 0 °C

With 1H-imidazole; N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja035445c