2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

Base Information

Chemical Name:2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol
CAS No.:939438-16-1
Molecular Formula:C₂₂H₃₅IO₄Si
Molecular Weight:518.507
Hs Code.:

Synonyms:2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

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Chemical Property of 2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

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Technology Process of 2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

There total 7 articles about 2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol 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: 84.0%

: 939438-06-9
(+/-)-(2-iodo-4-methoxy-3-(2-vinylcyclohex-2-enyloxy)benzyloxy)(tert-butyl)dimethylsilane

: 939438-16-1
2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

Guidance literature:: (+/-)-(2-iodo-4-methoxy-3-(2-vinylcyclohex-2-enyloxy)benzyloxy)(tert-butyl)dimethylsilane; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 15h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 3h; Further stages.;
DOI:10.1021/ol070255i

Reference yield:

: 939438-03-6
(+/-)-3-[1-(1-ethynyl-5-hexenyl)oxy]-2-iodo-4-methoxybenzaldehyde

: 939438-16-1
2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 62 percent / (PCy₃)2Ru(=CH-Ph)Cl₂ / CH₂Cl₂ / 12 h / Heating

2.1: NaBH₄ / methanol

3.1: 95 percent / DMAP; imidazole; Et₃N / CH₂Cl₂ / 12 h

4.1: 9-BBN / tetrahydrofuran / 15 h / 20 °C

4.2: 84 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol070255i

Reference yield:

: 764-59-0
hex-5-en-1-al

: 939438-16-1
2-(6-(3-((tert-butyldimethylsilyloxy)methyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 45 percent / tetrahydrofuran / -60 - 20 °C

2.1: 56 percent / n-Bu₃P; DBAD / tetrahydrofuran / 15 h

3.1: 62 percent / (PCy₃)2Ru(=CH-Ph)Cl₂ / CH₂Cl₂ / 12 h / Heating

4.1: NaBH₄ / methanol

5.1: 95 percent / DMAP; imidazole; Et₃N / CH₂Cl₂ / 12 h

6.1: 9-BBN / tetrahydrofuran / 15 h / 20 °C

6.2: 84 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; dibenzyl azodicarboxylate; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2.1: Mitsunobu coupling;
DOI:10.1021/ol070255i