(S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester

Base Information

• Chemical Name: (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester
• CAS No.: 875668-23-8
• Molecular Formula: C₂₆H₃₃N₂O₉P
• Molecular Weight: 548.53
• Mol file: 875668-23-8.mol

Synonyms:(S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property of (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester

There total 6 articles about (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl 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:

pivaloyloxymethyl (2S)-N-[p-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-2-vinylglycine (875668-22-7) → (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester (875668-23-8)

Guidance literature:

With ammonium hypophosphite; triethyl borane; In methanol; hexane; at 20 ℃; for 3h;

DOI:10.1021/jm050871p

Reference yield:

methyl (2S)-4-bromo-2-N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]aminobutyrate (875668-08-9) → (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester (875668-23-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaBH₄ / ethanol

1.2: 90 percent / ethanol / 0.5 h

2.1: aq. LiOH / methanol; CH₂Cl₂ / 2 h / 20 °C

3.1: 276 mg / dimethyl methylphosphonate; Ag₂CO₃ / dimethylformamide / 20 °C

4.1: 90 percent / aq. H₂O₂ / tetrahydrofuran / 1 h / Heating

5.1: ammonium hypophosphite; Et₃B / methanol; hexane / 3 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; ammonium hypophosphite; triethyl borane; dihydrogen peroxide; silver carbonate; dimethyl methane phosphonate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050871p

Reference yield:

methyl (2S)-2-N-[4-(N-carbobenzyloxy-N-methyl)aminobenzoyl]amino-4-(phenylselenyl)butyrate (875668-19-2) → (S)-2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-4-hydroxyphosphinoyl-butyric acid 2,2-dimethyl-propionyloxymethyl ester (875668-23-8)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. LiOH / methanol; CH₂Cl₂ / 2 h / 20 °C

2: 276 mg / dimethyl methylphosphonate; Ag₂CO₃ / dimethylformamide / 20 °C

3: 90 percent / aq. H₂O₂ / tetrahydrofuran / 1 h / Heating

4: ammonium hypophosphite; Et₃B / methanol; hexane / 3 h / 20 °C

With lithium hydroxide; ammonium hypophosphite; triethyl borane; dihydrogen peroxide; silver carbonate; dimethyl methane phosphonate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050871p

upstream raw materials:

pivaloyloxymethyl (2S)-N-[p-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-2-vinylglycine

methyl (2S)-4-bromo-2-N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]aminobutyrate

methyl (2S)-2-N-[4-(N-carbobenzyloxy-N-methyl)aminobenzoyl]amino-4-(phenylselenyl)butyrate

(2S)-2-N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]amino-4-(phenylselenyl)butyric acid

Downstream raw materials:

2-{[(S)-3-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-3-(2,2-dimethyl-propionyloxymethoxycarbonyl)-propyl]-hydroxy-phosphinoylmethyl}-pentanedioic acid bis-(2,2-dimethyl-propionyloxymethyl) ester

2-{[(S)-3-(2,2-Dimethyl-propionyloxymethoxycarbonyl)-3-(4-methylamino-benzoylamino)-propyl]-methoxy-phosphinoylmethyl}-pentanedioic acid bis-(2,2-dimethyl-propionyloxymethyl) ester

2-{[(S)-3-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-3-(2,2-dimethyl-propionyloxymethoxycarbonyl)-propyl]-methoxy-phosphinoylmethyl}-pentanedioic acid bis-(2,2-dimethyl-propionyloxymethyl) ester