(4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline

Base Information

• Chemical Name: (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline
• CAS No.: 372119-42-1
• Molecular Formula: C₁₉H₂₉NO₂Si
• Molecular Weight: 331.53
• Mol file: 372119-42-1.mol

Synonyms:(4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline

Chemical Property of (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline

There total 5 articles about (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline 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:

(4R)-3-benzoyl-4-tert-butyldimethylsilyloxymethyl-5-(2-propenyl)oxazolidin-2-one → (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline (372119-42-1)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 50 ℃; for 4h;

DOI:10.1021/jo015760m

Reference yield:

(R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester (112418-19-6) → (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline (372119-42-1)

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminum hydride / toluene / 3 h / -78 °C

2: tetrahydrofuran / 0 - 20 °C

3: NaH / tetrahydrofuran / 0 - 20 °C

4: NaH / tetrahydrofuran / 0 - 20 °C

5: 1,3-bis(diphenylphosphino)propane / Pd₂(dibenzylideneacetone)3CHCl₃ / tetrahydrofuran / 4 h / 50 °C

With 1,3-bis-(diphenylphosphino)propane; sodium hydride; diisobutylaluminium hydride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; toluene;

DOI:10.1021/jo015760m

Reference yield:

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate (124085-68-3) → (4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline (372119-42-1)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 0 - 20 °C

2: NaH / tetrahydrofuran / 0 - 20 °C

3: NaH / tetrahydrofuran / 0 - 20 °C

4: 1,3-bis(diphenylphosphino)propane / Pd₂(dibenzylideneacetone)3CHCl₃ / tetrahydrofuran / 4 h / 50 °C

With 1,3-bis-(diphenylphosphino)propane; sodium hydride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran;

DOI:10.1021/jo015760m

upstream raw materials:

(R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

Downstream raw materials:

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-4-methyloct-6-en-1-ol

(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene