L-Lysinamide, N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-N-[(1S)-1-(carboxymethyl)-3-[ (2,6-dimethylbenzoyl)oxy]-2-oxopropyl]-

Base Information

• Chemical Name: L-Lysinamide, N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-N-[(1S)-1-(carboxymethyl)-3-[ (2,6-dimethylbenzoyl)oxy]-2-oxopropyl]-
• CAS No.: 921771-35-9
• Molecular Formula: C33H42N4O11
• Molecular Weight: 670.717
• Mol file: 921771-35-9.mol

Synonyms:

Chemical Property of L-Lysinamide, N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-N-[(1S)-1-(carboxymethyl)-3-[ (2,6-dimethylbenzoyl)oxy]-2-oxopropyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Lysinamide, N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-N-[(1S)-1-(carboxymethyl)-3-[ (2,6-dimethylbenzoyl)oxy]-2-oxopropyl]-

There total 9 articles about L-Lysinamide, N-[(phenylmethoxy)carbonyl]-L-a-glutamyl-N-[(1S)-1-(carboxymethyl)-3-[ (2,6-dimethylbenzoyl)oxy]-2-oxopropyl]- 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: 80.0%

2,6-dimethyl-benzoic acid 3-[2-(2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-6-tert-butoxycarbonylamino-hexanoylamino]-4-ethoxycarbonyl-2-oxo-butyl ester (921771-34-8) → 2,6-dimethyl-benzoic acid 3-[6-amino-2-(2-benzyloxycarbonylamino-4-carboxy-butyrylamino)-hexanoylamino]-4-carboxy-2-oxo-butyl ester (921771-35-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 0 - 20 ℃; for 12h;

DOI:10.1021/jm060385h

Reference yield:

R-3-(2,2-dimethyl[1,3]dioxolan-4-yl)-acrylic acid ethyl ester (917877-01-1) → 2,6-dimethyl-benzoic acid 3-[6-amino-2-(2-benzyloxycarbonylamino-4-carboxy-butyrylamino)-hexanoylamino]-4-carboxy-2-oxo-butyl ester (921771-35-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 75 percent / 48 h / -50 °C

2: 86 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

3: 85 percent / CH₂Cl₂ / 12 h / 20 °C

4: 92 percent / H₂ / Pd/C / methanol / 4 h / atmospheric pressure

5: 81 percent / CH₂Cl₂ / 12 h / 20 °C

6: 70 percent / montmorillonite K₁₀ / ethanol; H₂O / 3 h / 75 °C

7: 72 percent / DMAP; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; pyridine / 72 h / 20 °C

8: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 20 °C

9: 80 percent / TFA / H₂O; CH₂Cl₂ / 12 h / 0 - 20 °C

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Montmorillonite K₁₀; hydrogen; Dess-Martin periodane; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jm060385h

Reference yield:

3-benzylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid ethyl ester (165133-39-1) → 2,6-dimethyl-benzoic acid 3-[6-amino-2-(2-benzyloxycarbonylamino-4-carboxy-butyrylamino)-hexanoylamino]-4-carboxy-2-oxo-butyl ester (921771-35-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

2: 85 percent / CH₂Cl₂ / 12 h / 20 °C

3: 92 percent / H₂ / Pd/C / methanol / 4 h / atmospheric pressure

4: 81 percent / CH₂Cl₂ / 12 h / 20 °C

5: 70 percent / montmorillonite K₁₀ / ethanol; H₂O / 3 h / 75 °C

6: 72 percent / DMAP; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; pyridine / 72 h / 20 °C

7: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 20 °C

8: 80 percent / TFA / H₂O; CH₂Cl₂ / 12 h / 0 - 20 °C

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Montmorillonite K₁₀; hydrogen; Dess-Martin periodane; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jm060385h

upstream raw materials:

2,6-dimethyl-benzoic acid 3-[2-(2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-6-tert-butoxycarbonylamino-hexanoylamino]-4-ethoxycarbonyl-2-oxo-butyl ester

R-3-(2,2-dimethyl[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

3-benzylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid ethyl ester

3-(2-amino-6-tert-butoxycarbonylamino-hexanoylamino)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid ethyl ester