(S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide

Base Information

• Chemical Name: (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide
• CAS No.: 845512-74-5
• Molecular Formula: C₂₆H₃₆N₆O₅
• Molecular Weight: 512.609
• Mol file: 845512-74-5.mol

Synonyms:

Chemical Property of (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide

There total 4 articles about (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide 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:

2,2,2-Trichloro-acetimidic acid (2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl ester → (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide (845512-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / NaOH / ethanol; H₂O / Heating

2: 50 percent / 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide*HCl; 1-hydroxybenztriazole; Et₃N / DMAP / dimethylformamide / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.11.109

Reference yield:

2,2,2-Trichloro-acetimidic acid (2S,3S,6S)-2-allyloxy-6-methanesulfonyloxymethyl-3,6-dihydro-2H-pyran-3-yl ester → (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide (845512-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃; Et₃N / dimethylformamide / 60 °C

2: 64 percent / NaOH / ethanol; H₂O / Heating

3: 50 percent / 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide*HCl; 1-hydroxybenztriazole; Et₃N / DMAP / dimethylformamide / 20 °C

With sodium hydroxide; sodium azide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.11.109

Reference yield:

2,2,2-trichloro-acetimidic acid 6-allyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester (845512-69-8) → (S)-2-Acetylamino-4-methyl-pentanoic acid [(S)-1-((2S,3S,6S)-2-allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-ylcarbamoyl)-2-phenyl-ethyl]-amide (845512-74-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / K₂CO₃ / xylene / Heating

2: 80 percent / TBAF*3H₂O / tetrahydrofuran

3: Et₃N / CH₂Cl₂ / 0 °C

4: NaN₃; Et₃N / dimethylformamide / 60 °C

5: 64 percent / NaOH / ethanol; H₂O / Heating

6: 50 percent / 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide*HCl; 1-hydroxybenztriazole; Et₃N / DMAP / dimethylformamide / 20 °C

With sodium hydroxide; sodium azide; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene; 1: Overman rearrangement;

DOI:10.1016/j.tetlet.2004.11.109

upstream raw materials:

2,2,2-trichloro-acetimidic acid 6-allyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester