(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

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)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester
• CAS No.: 1027309-65-4
• Molecular Formula: C₃₈H₅₃N₂O₁₁P
• Molecular Weight: 744.819
• Mol file: 1027309-65-4.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)-2-methyl-1-(2-oxo-ethyl)-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)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester

There total 24 articles about (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 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:

(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)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester (1027309-65-4)

Guidance literature:

Multi-step reaction with 7 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

7: Dess-Martin periodinane

With dmap; formic acid; Isopropenyl chloroformate; diethyl cyanophosphonate; water-soluble carbodiimide*HCl; boron trifluoride diethyl etherate; hydrogen; Dess-Martin periodane; 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)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester (1027309-65-4)

Guidance literature:

Multi-step reaction with 6 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

6: Dess-Martin periodinane

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

DOI:10.1248/cpb.42.2394

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → (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 (1027309-65-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / 1N aq. H₂SO₄, NaNO₂

2: diethyl ether

3: TfOH / diethyl ether

4: 88 percent / 1N aq. KOH / dioxane

5: (COCl)2

6: 90 percent / NEt₃, DMAP / CH₂Cl₂

7: isopropenyl chloroformate, NEt₃, DMAP / CH₂Cl₂

8: 85 percent / n-BuNF, AcOH

9: Dess-Martin periodinane

With dmap; potassium hydroxide; oxalyl dichloride; Isopropenyl chloroformate; trifluorormethanesulfonic acid; sulfuric acid; Dess-Martin periodane; acetic acid; triethylamine; sodium nitrite; In 1,4-dioxane; diethyl ether; dichloromethane;

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-hydroxy-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:

desepoxyarenastatin A

cryptophycin-24

arenastatin A