(2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester

Base Information

• Chemical Name: (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester
• CAS No.: 503560-07-4
• Molecular Formula: C₂₀H₂₉NO₄Si
• Molecular Weight: 375.54
• Mol file: 503560-07-4.mol

Synonyms:(2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester

Chemical Property of (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester

There total 4 articles about (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic 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:

(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline (208935-32-4) → (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester (503560-07-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / methanol / -78 °C

2.1: LiCl; DBU / acetonitrile / 1 h

2.2: 2.03 g / acetonitrile / 2 h

With ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In methanol; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

Reference yield:

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide (503560-10-9) → (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester (503560-07-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 99 percent / pyridine / CH₂Cl₂ / 12 h

3.1: 75 percent / K₂CO₃; Pd(PPh₃)4 / acetonitrile / 24 h / Heating

4.1: O₃ / methanol / -78 °C

5.1: LiCl; DBU / acetonitrile / 1 h

5.2: 2.03 g / acetonitrile / 2 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

Reference yield:

N-((1S)-2-acetoxy-1-(tert-butyldimethylsilanyloxymethyl)-3-butenyl)-benzamide (497227-95-9) → (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester (503560-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / K₂CO₃; Pd(PPh₃)4 / acetonitrile / 24 h / Heating

2.1: O₃ / methanol / -78 °C

3.1: LiCl; DBU / acetonitrile / 1 h

3.2: 2.03 g / acetonitrile / 2 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In methanol; acetonitrile;

DOI:10.1016/S0957-4166(02)00794-2

upstream raw materials:

(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide

N-((1S)-2-acetoxy-1-(tert-butyldimethylsilanyloxymethyl)-3-butenyl)-benzamide

Downstream raw materials:

3-((4S,trans)-4,5-dihydro-4-methyl-2-phenyloxazol-5-yl)-heptadecan-3-one-16-ethylenacetal

3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-N-methoxy-N-methyl-propionamide

3-[(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-propionic acid

3-(4-iodomethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide