6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

Base Information

Chemical Name:6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile
CAS No.:276679-45-9
Molecular Formula:C₃₃H₄₈INO₂Si₂
Molecular Weight:673.825
Hs Code.:

6-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

Synonyms:6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

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Chemical Property of 6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

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Technology Process of 6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

There total 9 articles about 6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile 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: 98.0%

: 276679-43-7
[(E)-(R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-((Z)-3-iodo-allyl)-5-methyl-hex-4-en-(E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine

: 276679-45-9
6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

Guidance literature:: With magnesium monoperoxyphthalate hexahydrate; In methanol; diethyl ether; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja000728f

Reference yield:

: [6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-hex-4-enylidene]-(2-methoxymethyl-pyrrolidin-1-yl)-amine

: 276679-45-9
6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 24 h / 0 °C

1.2: tetrahydrofuran; hexane / -100 - 0 °C

2.1: 98 percent / magnesium monoperoxyphthalate hexahydrate / methanol; diethyl ether / 0.08 h / 0 °C

With magnesium monoperoxyphthalate hexahydrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; 1.1: Metallation / 1.2: Alkylation / 2.1: Oxidation;
DOI:10.1021/ja000728f

Reference yield:

: 1026915-69-4
2-[1-Methyl-2-oxo-eth-(E)-ylidene]-pentanedioic acid 1-ethyl ester 5-methyl ester

: 276679-45-9
6-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-(3-iodo-allyl)-5-methyl-hex-4-enenitrile

Guidance literature:: Multi-step reaction with 9 steps

1.1: 7.013 g / NaBH₄ / methanol; CH₂Cl₂ / 1 h

2.1: 95 percent / imidazole; N,N-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 96 percent / NaOH / tetrahydrofuran; H₂O / 5 °C

4.1: carbonyldiimidazole / CH₂Cl₂ / 3 h / 23 °C

4.2: 89 percent / Et₃N / CH₂Cl₂ / 23 °C

5.1: DIBALH / CH₂Cl₂ / 7 h / -78 °C

5.2: 89 percent / CH₂Cl₂

6.1: 93 percent / PTSA / benzene / 48 h / Heating

7.1: 100 percent / imidazole / CH₂Cl₂ / 0.5 h

8.1: LDA / tetrahydrofuran; hexane / 24 h / 0 °C

8.2: tetrahydrofuran; hexane / -100 - 0 °C

9.1: 98 percent / magnesium monoperoxyphthalate hexahydrate / methanol; diethyl ether / 0.08 h / 0 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; benzene; 1.1: Reduction / 2.1: silylation / 3.1: Hydrolysis / 4.1: Substitution / 4.2: Substitution / 5.1: Reduction / 5.2: Cyclization / 6.1: Condensation / 7.1: silylation / 8.1: Metallation / 8.2: Alkylation / 9.1: Oxidation;
DOI:10.1021/ja000728f