N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester

Base Information

• Chemical Name: N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester
• CAS No.: 269411-10-1
• Molecular Formula: C₄₅H₇₇N₅O₉
• Molecular Weight: 832.134
• Mol file: 269411-10-1.mol

Synonyms:

Chemical Property of N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester

There total 13 articles about N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-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:

ethyl 3-oxotetradecanoate (74124-22-4) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester (269411-10-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: hydrogen; RuCl₂[(S)-BINAP]; HCl / methanol / 3800.26 - 4560.31 Torr

2.1: LiOH / tetrahydrofuran; methanol; H₂O

3.1: 96 percent / benzotriazol-1-yloxy-tris(dimethylamino)phosphonium chloride; ethyldiisopropylamine / CH₂Cl₂

4.1: 46 percent / diethyl azodicarboxylate; triphenylphosphane / tetrahydrofuran

5.1: LiHMDS / tetrahydrofuran

5.2: 93 percent / tetrahydrofuran

6.1: ammonium cerium(IV) nitrate / acetonitrile; H₂O

7.1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

8.1: sodium hydroxide / tetrahydrofuran; H₂O

9.1: 91 percent / WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / dimethylformamide

10.1: trifluoroacetic acid / CH₂Cl₂

11.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

12.1: trifluoroacetic acid / CH₂Cl₂

13.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

With hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; ammonium cerium(IV) nitrate; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); WSCD*HCl; hydrogen; benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium chloride; 1-hydroxybenzotriazol-hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Reduction / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Cyclization / 5.1: Metallation / 5.2: Methylation / 6.1: dearylation / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Acylation / 10.1: Hydrolysis / 11.1: Acylation / 12.1: Hydrolysis / 13.1: Acylation;

DOI:10.1021/ol005630k

Reference yield:

(3S)-3-hydroxytetradecanoic acid (35683-15-9,3422-31-9) → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester (269411-10-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 96 percent / benzotriazol-1-yloxy-tris(dimethylamino)phosphonium chloride; ethyldiisopropylamine / CH₂Cl₂

2.1: 46 percent / diethyl azodicarboxylate; triphenylphosphane / tetrahydrofuran

3.1: LiHMDS / tetrahydrofuran

3.2: 93 percent / tetrahydrofuran

4.1: ammonium cerium(IV) nitrate / acetonitrile; H₂O

5.1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

6.1: sodium hydroxide / tetrahydrofuran; H₂O

7.1: 91 percent / WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / dimethylformamide

8.1: trifluoroacetic acid / CH₂Cl₂

9.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

10.1: trifluoroacetic acid / CH₂Cl₂

11.1: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

With dmap; sodium hydroxide; ammonium cerium(IV) nitrate; WSCD*HCl; benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium chloride; 1-hydroxybenzotriazol-hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Acylation / 2.1: Cyclization / 3.1: Metallation / 3.2: Methylation / 4.1: dearylation / 5.1: Acylation / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Acylation / 10.1: Hydrolysis / 11.1: Acylation;

DOI:10.1021/ol005630k

Reference yield:

(3R,4R)-3-Methyl-4-undecyl-azetidin-2-one → N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]-glycine ethyl ester (269411-10-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

2: sodium hydroxide / tetrahydrofuran; H₂O

3: 91 percent / WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / dimethylformamide

4: trifluoroacetic acid / CH₂Cl₂

5: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

6: trifluoroacetic acid / CH₂Cl₂

7: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

With dmap; sodium hydroxide; WSCD*HCl; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Acylation / 4: Hydrolysis / 5: Acylation / 6: Hydrolysis / 7: Acylation;

DOI:10.1021/ol005630k

upstream raw materials:

Boc-Lys(Z)-OH

ethyl 3-oxotetradecanoate

(3S)-3-hydroxytetradecanoic acid

(S)-ethyl 3-hydroxytetradecanoate