(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester
CAS No.:213182-19-5
Molecular Formula:C₃₉H₆₀O₅Si₂
Molecular Weight:665.073
Hs Code.:

(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

Synonyms:(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

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Chemical Property of (1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

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Technology Process of (1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

There total 10 articles about (1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester 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%

: 67-56-1
methanol

: 144446-55-9
(2R,5S,6R,9R)-2-tert-Butyl-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-one

: 213182-19-5
(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: With potassium carbonate; In tetrahydrofuran; for 6h;
DOI:10.1021/jo980379w

Reference yield:

: 129144-88-3
2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2(E)-butenal

: 213182-19-5
(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / PPh₃ / CH₂Cl₂ / 0 - 20 °C

2: Pd(PPh₃)4 / tetrahydrofuran; H₂O / 0.33 h

3: 90 percent / Et₃N / CH₂Cl₂ / 2 h

4: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -100 °C

5: 72 percent / BHT / trichloroethene / 110 - 120 °C

6: 85 percent / K₂CO₃ / tetrahydrofuran / 6 h

With n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; Trichloroethylene; water;
DOI:10.1021/jo980379w

Reference yield:

: 144446-52-6
tert-Butyl-[(Z)-2-(2,2-dibromo-vinyl)-but-2-enyloxy]-diphenyl-silane

: 213182-19-5
(1S,2R,5R)-2-[(E)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-1-enyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Pd(PPh₃)4 / tetrahydrofuran; H₂O / 0.33 h

2: 90 percent / Et₃N / CH₂Cl₂ / 2 h

3: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -100 °C

4: 72 percent / BHT / trichloroethene / 110 - 120 °C

5: 85 percent / K₂CO₃ / tetrahydrofuran / 6 h

With n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; Trichloroethylene; water;
DOI:10.1021/jo980379w