(2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid

Base Information

• Chemical Name: (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid
• CAS No.: 623937-24-6
• Molecular Formula: C₄₅H₆₉N₃O₈
• Molecular Weight: 780.058
• Mol file: 623937-24-6.mol

Synonyms:(2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid

Chemical Property of (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid

There total 4 articles about (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid 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: 99.0%

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid (623937-22-4) → (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid (623937-24-6)

Guidance literature:

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid; With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 0.5h;

With sodium hydrogencarbonate; sodium carbonate; In dichloromethane;

DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

(E)-(4R,5R)-5-Hydroxy-4-methyl-octadec-2-enoic acid allyl ester (623937-14-4) → (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid (623937-24-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

2.1: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

3.1: 81 percent / EDCI; HOBt / CH₂Cl₂ / 0.5 h / 25 °C

4.1: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

5.1: TFA / CH₂Cl₂ / 0.5 h / 25 °C

5.2: 99 percent / NaHCO₃; Na₂CO₃ / CH₂Cl₂

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.013

Reference yield:

(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-enoic acid allyl ester (623937-12-2) → (2S,3R)-2-{(S)-2-[(E)-(4R,5R)-5-((S)-2-Amino-3-benzyloxy-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-3-benzyloxy-butyric acid (623937-24-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / HF*Pyr / tetrahydrofuran / 12 h / 25 °C

2.1: 82 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

3.1: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

4.1: 81 percent / EDCI; HOBt / CH₂Cl₂ / 0.5 h / 25 °C

5.1: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

6.1: TFA / CH₂Cl₂ / 0.5 h / 25 °C

6.2: 99 percent / NaHCO₃; Na₂CO₃ / CH₂Cl₂

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.013

upstream raw materials:

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(E)-(4R,5R)-5-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoylamino]-3-methyl-butyrylamino}-butyric acid

(E)-(4R,5R)-5-Hydroxy-4-methyl-octadec-2-enoic acid allyl ester

(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-octadec-2-enoic acid allyl ester

(E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid allyl ester