[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

Base Information

• Chemical Name: [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester
• CAS No.: 371149-20-1
• Molecular Formula: C₂₂H₄₂O₅Si₂
• Molecular Weight: 442.743
• Mol file: 371149-20-1.mol

Synonyms:[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

Chemical Property of [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

There total 4 articles about [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl 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:

ethyl iodide (75-03-6) + [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid → [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester (371149-20-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(00)00170-2

Reference yield:

acetic acid 5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-4,5,6,7-tetrahydro-2H-benzofuran-7a-yl ester (273402-85-0) → [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester (371149-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol / 1 h / 20 °C

2: K₂CO₃ / dimethylformamide / 4 h / 20 °C

With potassium carbonate; In methanol; N,N-dimethyl-formamide; 1: Ring cleavage / 2: Esterification;

DOI:10.1016/S0040-4039(00)00170-2

Reference yield:

[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-oxo-cyclohexyl]-acetic acid tert-butyl ester (273402-79-2) → [(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-(Z)-ylidene]-acetic acid ethyl ester (371149-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / Sc(OTf)3 / acetonitrile / 12 h / 20 °C

2: DBU / CH₂Cl₂ / 0.5 h / 20 °C

3: K₂CO₃ / methanol / 1 h / 20 °C

4: K₂CO₃ / dimethylformamide / 4 h / 20 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Cyclization / 2: Elimination / 3: Ring cleavage / 4: Esterification;

DOI:10.1016/S0040-4039(00)00170-2

upstream raw materials:

ethyl iodide

acetic acid 5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-4,5,6,7-tetrahydro-2H-benzofuran-7a-yl ester

[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-oxo-cyclohexyl]-acetic acid tert-butyl ester

Acetic acid (5S,7S)-3a-acetoxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-oxo-hexahydro-benzofuran-7a-yl ester

Downstream raw materials:

<3S-(1Z,3α,5β)>-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid ethyl ester