(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester

Base Information

• Chemical Name: (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester
• CAS No.: 725240-18-6
• Molecular Formula: C₃₂H₄₁N₃O₈
• Molecular Weight: 595.693
• Mol file: 725240-18-6.mol

Synonyms:(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester

Chemical Property of (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester

There total 11 articles about (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic 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:

(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid (725240-16-4) + (S)-6-Amino-2-((S)-2-benzyloxycarbonylamino-propionylamino)-hexanoic acid benzyl ester; hydrochloride → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester (725240-18-6)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; thymidine 5'-phosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; at -30 - 20 ℃; for 36h;

DOI:10.1021/ol049409+

Reference yield:

(3S)-methylvaleric acid (1730-92-3) → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester (725240-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / DCC; DMAP / CH₂Cl₂ / 1 h / Heating

2.1: 92 percent / n-BuLi; HTMP / tetrahydrofuran / -78 - 20 °C

3.1: Sn(OTf)2; BOX / CH₂Cl₂ / -78 - 20 °C

3.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

3.3: 0.46 g / aq. HCl / dioxane / 51 h / 60 °C

4.1: 0.26 g / HOAt; TMP; EDC / dimethylformamide; CH₂Cl₂ / 36 h / -30 - 20 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; tin(II) trifluoromethanesulfonate; n-butyllithium; 1-hydroxy-7-aza-benzotriazole; thymidine 5'-phosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol049409+

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}hexanoic acid benzyl ester (725240-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / hydroxylamine-O-sulfonic acid; aq. NaOH / 27 h / 20 - 100 °C

2.1: 97 percent / DCC; DMAP / CH₂Cl₂ / 1 h / Heating

3.1: 92 percent / n-BuLi; HTMP / tetrahydrofuran / -78 - 20 °C

4.1: Sn(OTf)2; BOX / CH₂Cl₂ / -78 - 20 °C

4.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

4.3: 0.46 g / aq. HCl / dioxane / 51 h / 60 °C

5.1: 0.26 g / HOAt; TMP; EDC / dimethylformamide; CH₂Cl₂ / 36 h / -30 - 20 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; sodium hydroxide; tin(II) trifluoromethanesulfonate; n-butyllithium; 1-hydroxy-7-aza-benzotriazole; thymidine 5'-phosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; hydroxylamine-O-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol049409+

upstream raw materials:

(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid

(3S)-methylvaleric acid

L-isoleucine

N-Cbz-Ala