N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester

Base Information

• Chemical Name: N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester
• CAS No.: 172941-98-9
• Molecular Formula: C₃₉H₆₅N₅O₉
• Molecular Weight: 747.973

Synonyms:N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester

Chemical Property of N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester

There total 4 articles about N²-tert-butoxycarbonyl-N⁵-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl 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:

Boc-L-Val-3(R)-aminododecanoic acid methyl ester (172941-77-4) → N2-tert-butoxycarbonyl-N5-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester (172941-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiOH / tetrahydrofuran; methanol; H₂O

2: WSCD*HCl; 1-hydroxybenzotriazole hydrate; triethylamine / tetrahydrofuran; dimethylformamide

3: trifluoroacetic acid / CH₂Cl₂

4: WSCD*HCl; 1-hydroxybenzotriazole hydrate; triethylamine / tetrahydrofuran

With lithium hydroxide; WSCD*HCl; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Condensation / 3: Hydrolysis / 4: Condensation;

DOI:10.1021/ol005631c

Reference yield:

(R)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-dodecanoic acid (172941-94-5) → N2-tert-butoxycarbonyl-N5-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester (172941-98-9)

Guidance literature:

Multi-step reaction with 3 steps

1: WSCD*HCl; 1-hydroxybenzotriazole hydrate; triethylamine / tetrahydrofuran; dimethylformamide

2: trifluoroacetic acid / CH₂Cl₂

3: WSCD*HCl; 1-hydroxybenzotriazole hydrate; triethylamine / tetrahydrofuran

With WSCD*HCl; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation;

DOI:10.1021/ol005631c

Reference yield:

[(R)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-dodecanoylamino]-acetic acid ethyl ester (172941-95-6) → N2-tert-butoxycarbonyl-N5-benzyloxycarbonylornithyl-valyl-((R)-3-nonyl-β-alanyl)-glycine ethyl ester (172941-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / CH₂Cl₂

2: WSCD*HCl; 1-hydroxybenzotriazole hydrate; triethylamine / tetrahydrofuran

With WSCD*HCl; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Condensation;

DOI:10.1021/ol005631c

upstream raw materials:

Boc-Orn(Z)-OH

valyl-((R)-3-nonyl-β-alanyl)-glycine-ethyl ester

Boc-L-Val-3(R)-aminododecanoic acid methyl ester

(R)-3-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-dodecanoic acid

Downstream raw materials:

{(R)-3-[(S)-2-((S)-2-Amino-5-benzyloxycarbonylamino-pentanoylamino)-3-methyl-butyrylamino]-dodecanoylamino}-acetic acid

[3-((5S,8S,11R)-8-Isopropyl-11-nonyl-3,6,9,13-tetraoxo-1,4,7,10-tetraaza-cyclotridec-5-yl)-propyl]-carbamic acid benzyl ester

{(R)-3-[(S)-2-((S)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentanoylamino)-3-methyl-butyrylamino]-dodecanoylamino}-acetic acid

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