tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate

Base Information

• Chemical Name: tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate
• CAS No.: 756531-78-9
• Molecular Formula: C₃₆H₄₂N₂O₇
• Molecular Weight: 614.739
• Mol file: 756531-78-9.mol

Synonyms:tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate

Chemical Property of tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate

There total 4 articles about tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate 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:

glutaric anhydride, (108-55-4) → tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate (756531-78-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 24 percent / NEt₃; DMAP; N-hydroxysuccinimide / toluene / 24 h / Heating

2.1: tBuCOCl; NEt₃ / tetrahydrofuran / 2 h / -30 °C

2.2: 90 percent / LiCl / tetrahydrofuran / -30 - 20 °C

3.1: LHDMS / tetrahydrofuran / 1 h / -78 °C

3.2: 55 percent / tetrahydrofuran / 20 h / -50 °C

4.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

5.1: Et₃N; DPPA / toluene

5.2: 75 percent / toluene / 16 h / Heating

With dmap; 1-hydroxy-pyrrolidine-2,5-dione; diphenyl-phosphinic acid; hydrogen; pivaloyl chloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1002/hlca.200490142

Reference yield:

5-(tert-butoxy)-5-oxopentanoic acid (63128-51-8) → tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate (756531-78-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tBuCOCl; NEt₃ / tetrahydrofuran / 2 h / -30 °C

1.2: 90 percent / LiCl / tetrahydrofuran / -30 - 20 °C

2.1: LHDMS / tetrahydrofuran / 1 h / -78 °C

2.2: 55 percent / tetrahydrofuran / 20 h / -50 °C

3.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

4.1: Et₃N; DPPA / toluene

4.2: 75 percent / toluene / 16 h / Heating

With diphenyl-phosphinic acid; hydrogen; pivaloyl chloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1002/hlca.200490142

Reference yield:

(R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-13-4) → tert-butyl (S)-4-({[(benzyloxy)carbonyl]amino}methyl)-5-[(R)-4-(1-methylethyl)-2-oxo-5,5-diphenyloxazolidin-3-yl]-4-oxopentanoate (756531-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

2.1: Et₃N; DPPA / toluene

2.2: 75 percent / toluene / 16 h / Heating

With diphenyl-phosphinic acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; toluene;

DOI:10.1002/hlca.200490142

upstream raw materials:

glutaric anhydride,

5-(tert-butoxy)-5-oxopentanoic acid

(R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

(R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

Downstream raw materials:

(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-[(tert-butoxy)carbonyl]butanoic acid

benzyl (S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-{[(triphenylmethyl)amino]carbonyl}butanoate

1-benzyl 5-(tert-butyl) (S)-2-({[(benzyloxy)carbonyl]amino}methyl)pentanedioate

benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate