Bicyclo[4.1.0]heptane-7-carboxylic acid, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[2-[(4-methoxyphenyl)methoxy] ethyl]-4-[(phenylmethoxy)methyl]-, ethyl ester, (3S,4S)-

Base Information

• Chemical Name: Bicyclo[4.1.0]heptane-7-carboxylic acid, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[2-[(4-methoxyphenyl)methoxy] ethyl]-4-[(phenylmethoxy)methyl]-, ethyl ester, (3S,4S)-
• CAS No.: 566163-71-1
• Molecular Formula: C34H50O6Si
• Molecular Weight: 582.853
• Mol file: 566163-71-1.mol

Synonyms:

Chemical Property of Bicyclo[4.1.0]heptane-7-carboxylic acid, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[2-[(4-methoxyphenyl)methoxy] ethyl]-4-[(phenylmethoxy)methyl]-, ethyl ester, (3S,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[4.1.0]heptane-7-carboxylic acid, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[2-[(4-methoxyphenyl)methoxy] ethyl]-4-[(phenylmethoxy)methyl]-, ethyl ester, (3S,4S)-

There total 5 articles about Bicyclo[4.1.0]heptane-7-carboxylic acid, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[2-[(4-methoxyphenyl)methoxy] ethyl]-4-[(phenylmethoxy)methyl]-, ethyl ester, (3S,4S)- 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: 96.0%

diazoacetic acid ethyl ester (623-73-4) + {(4S,5S)-4-Benzyloxymethyl-5-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-1-enyloxy}-tert-butyl-dimethyl-silane (565436-02-4) → (3S,4S)-4-Benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester (566163-71-1)

Guidance literature:

copper acetylacetonate; In ethyl acetate; at 110 ℃;

DOI:10.1016/S0040-4039(03)00835-9

Reference yield:

2-(tert-butyldimethylsiloxy)-1,3-butadiene (80738-05-2) → (3S,4S)-4-Benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester (566163-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / Et₂AlCl / CH₂Cl₂ / -78 - -20 °C

2: 51 percent / LiBH₄; EtOH / tetrahydrofuran / 0 - 20 °C

3: 60 percent / NaH; nBu₄NBr / tetrahydrofuran

4: 96 percent / Cu(acac)2 / ethyl acetate / 110 °C

With lithium borohydride; ethanol; tetrabutylammomium bromide; diethylaluminium chloride; sodium hydride; copper acetylacetonate; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Diels-Alder reaction;

DOI:10.1016/S0040-4039(03)00835-9

Reference yield:

(S)-4-Benzyl-3-[(E)-5-(4-methoxy-benzyloxy)-pent-2-enoyl]-oxazolidin-2-one → (3S,4S)-4-Benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester (566163-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / Et₂AlCl / CH₂Cl₂ / -78 - -20 °C

2: 51 percent / LiBH₄; EtOH / tetrahydrofuran / 0 - 20 °C

3: 60 percent / NaH; nBu₄NBr / tetrahydrofuran

4: 96 percent / Cu(acac)2 / ethyl acetate / 110 °C

With lithium borohydride; ethanol; tetrabutylammomium bromide; diethylaluminium chloride; sodium hydride; copper acetylacetonate; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Diels-Alder reaction;

DOI:10.1016/S0040-4039(03)00835-9

upstream raw materials:

diazoacetic acid ethyl ester

{(4S,5S)-4-Benzyloxymethyl-5-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-1-enyloxy}-tert-butyl-dimethyl-silane

2-(tert-butyldimethylsiloxy)-1,3-butadiene

(S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one

Downstream raw materials:

2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester