(2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester

Base Information

• Chemical Name: (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester
• CAS No.: 1025955-33-2
• Molecular Formula: C₄₃H₅₄N₆O₁₄
• Molecular Weight: 878.934

Synonyms:

Chemical Property of (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester

There total 13 articles about (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl 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:

(S)-2-((2R,3S)-2-Amino-3-hydroxy-butyrylamino)-propionic acid tert-butyl ester → (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester (1025955-33-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 48 h / Ambient temperature

2: 1.) CH₃O₂CNSO₂NEt₃, 2.) 1 N aq. HCl / 1.) THF, 70 deg C, 2 h, 2.) r.t., 30 min

3: H₂ / 10percent Pd/C / methanol / 3 h

4: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 20 h / Ambient temperature

5: TFA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogenchloride; Burgess Reagent; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; chloroform;

DOI:10.1021/jo00112a009

Reference yield:

(S)-2-((2R,3R)-2-Amino-3-hydroxy-butyrylamino)-propionic acid tert-butyl ester → (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester (1025955-33-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 48 h / Ambient temperature

2: H₂ / 10percent Pd/C / methanol / 3 h

3: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 20 h / Ambient temperature

4: TFA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; chloroform;

DOI:10.1021/jo00112a009

Reference yield:

N-Cbz-D-Threonyl-L-alanine tert-butyl ester (162553-97-1) → (2R,3R)-3-((S)-2,6-Bis-benzyloxycarbonylamino-hexanoylamino)-N-{(S)-1-[(1R,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-ethyl}-2-hydroxy-succinamic acid benzyl ester (1025955-33-2)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd/C / methanol / 3 h

2: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 48 h / Ambient temperature

3: 1.) CH₃O₂CNSO₂NEt₃, 2.) 1 N aq. HCl / 1.) THF, 70 deg C, 2 h, 2.) r.t., 30 min

4: H₂ / 10percent Pd/C / methanol / 3 h

5: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / CHCl₃ / 20 h / Ambient temperature

6: TFA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogenchloride; Burgess Reagent; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; chloroform;

DOI:10.1021/jo00112a009

upstream raw materials:

(Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanine tert-butyl ester

N_α,N_ε-bis(carbobenzyloxy)-L-lysine N-hydroxysuccinimide ester

N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine

β-Benzyl D-threo-β-hydroxyaspartate

Downstream raw materials:

(Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine

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