(S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester

Base Information

• Chemical Name: (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester
• CAS No.: 162473-77-0
• Molecular Formula: C₃₈H₅₅N₂O₁₁P
• Molecular Weight: 746.835
• Mol file: 162473-77-0.mol

Synonyms:

Chemical Property of (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester

There total 23 articles about (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl 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: 85.0%

(S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-4-phenyl-but-3-enyl ester (162473-76-9) → (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester (162473-77-0)

Guidance literature:

With acetic acid;

DOI:10.1248/cpb.42.2394

Reference yield:

(R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid (65806-89-5) → (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester (162473-77-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / diethyl phosphorocyanide, Et₃N / dimethylformamide

2: H₂, HCOOH / Pd/C / methanol

3: water-soluble carbodiimide*HCl, DMAP / tetrahydrofuran

4: BF₃*OEt₂ / acetonitrile

5: isopropenyl chloroformate, NEt₃, DMAP / CH₂Cl₂

6: 85 percent / n-BuNF, AcOH

With dmap; formic acid; Isopropenyl chloroformate; diethyl cyanophosphonate; water-soluble carbodiimide*HCl; boron trifluoride diethyl etherate; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.42.2394

Reference yield:

3-[(R)-2-Benzyloxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester (162472-69-7) → (S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-(2-hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enyl ester (162473-77-0)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂, HCOOH / Pd/C / methanol

2: water-soluble carbodiimide*HCl, DMAP / tetrahydrofuran

3: BF₃*OEt₂ / acetonitrile

4: isopropenyl chloroformate, NEt₃, DMAP / CH₂Cl₂

5: 85 percent / n-BuNF, AcOH

With dmap; formic acid; Isopropenyl chloroformate; water-soluble carbodiimide*HCl; boron trifluoride diethyl etherate; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.42.2394

upstream raw materials:

(S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-4-phenyl-but-3-enyl ester

L-leucine

(S)-2-hydroxyl-3,3-dimethylbutyric acid

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol

Downstream raw materials:

arenastatin A

cryptophycin-24

desepoxyarenastatin A

(S)-2-{3-[(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (E)-(1S,2R)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester