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

Base Information

• Chemical Name: (S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one
• CAS No.: 565436-17-1
• Molecular Formula: C₃₃H₄₅NO₆Si
• Molecular Weight: 579.809
• Mol file: 565436-17-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one 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: 81.0%

2-(tert-butyldimethylsiloxy)-1,3-butadiene (80738-05-2) + (S)-4-Benzyl-3-[(E)-5-(4-methoxy-benzyloxy)-pent-2-enoyl]-oxazolidin-2-one → (S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one (565436-17-1)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 - -20 ℃;

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

Reference yield: 51.0%

(S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one (565436-17-1) → {(1S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enyl}-methanol

Guidance literature:

With lithium borohydride; ethanol; In tetrahydrofuran; at 0 - 20 ℃;

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

Reference yield:

(S)-4-Benzyl-3-{(1S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enecarbonyl}-oxazolidin-2-one (565436-17-1) → 2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-2-bromo-malonic acid diethyl ester

Guidance literature:

Multi-step reaction with 5 steps

1.1: 51 percent / LiBH₄; EtOH / tetrahydrofuran / 0 - 20 °C

2.1: 60 percent / NaH; nBu₄NBr / tetrahydrofuran

3.1: 96 percent / Cu(acac)2 / ethyl acetate / 110 °C

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 12 h / -78 - 20 °C

4.3: 73 percent / TBAF / tetrahydrofuran

5.1: 92 percent / NaHMDS; NBS

With N-Bromosuccinimide; lithium borohydride; ethanol; tetrabutylammomium bromide; sodium hexamethyldisilazane; sodium hydride; lithium diisopropyl amide; copper acetylacetonate; In tetrahydrofuran; ethyl acetate;

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

upstream raw materials:

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

Downstream raw materials:

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

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

(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