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

Base Information

• Chemical Name: (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid
• CAS No.: 623937-18-8
• Molecular Formula: C₃₄H₅₅NO₇
• Molecular Weight: 589.813
• Mol file: 623937-18-8.mol

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

Chemical Property of (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid

There total 2 articles about (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic 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: 98.0%

(E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid allyl ester (623937-16-6) → (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid (623937-18-8)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 0.5h;

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) → (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid (623937-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 25 °C

2: 98 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 25 °C

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

DOI:10.1016/j.tetlet.2003.08.013

Reference yield: 81.0%

(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-benzyloxy-butyric acid allyl ester + (E)-(4R,5R)-5-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-4-methyl-octadec-2-enoic acid (623937-18-8) → (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 allyl ester (623937-20-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2003.08.013

upstream raw materials:

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

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

Downstream 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 allyl ester