Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce

Base Information

• Chemical Name: Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce
• CAS No.: 185461-53-4
• Molecular Formula: C₇₀H₁₀₉Cl₃N₆O₁₇Si
• Molecular Weight: 1441.11
• Mol file: 185461-53-4.mol

Synonyms:Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce

Chemical Property of Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce

There total 18 articles about Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce 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: 60.0%

Boc-(R)-MeLeu-(S)-Thr[Z-(S)-MeTyr(Me)]-(3S,4R,5S)-Ist(TBDMS)-OH (118171-89-4) + (S)-1-[(S)-2-((S)-4-Hydroxy-2,5-dimethyl-3-oxo-hexanoylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid 2,2,2-trichloro-ethyl ester (185461-62-5) → Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce (185461-53-4)

Guidance literature:

With 4-N,N-dimethylaminopyridine trifluoroacetate; diisopropyl-carbodiimide; In chloroform; 1.) reflux, 8 h, 2.) room temperature, 16 h;

DOI:10.1021/jo961932h

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce (185461-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / DMAP, DCC / CH₂Cl₂ / 7 h / 0 °C

2: TFA / CH₂Cl₂ / 0.33 h

3: 76 percent / 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / acetonitrile / 3 h / Ambient temperature

4: 78 percent / H₂ / Pd/C / tetrahydrofuran / 1 h / 760 Torr / Ambient temperature

5: 60 percent / DMAP*CF₃COOH, N,N'-diisopropylcarbodiimide / CHCl₃ / 1.) reflux, 8 h, 2.) room temperature, 16 h

With dmap; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen; benzotriazol-1-ol; 4-N,N-dimethylaminopyridine trifluoroacetate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo961932h

Reference yield:

H-Pro-OTce (126134-58-5) → Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce (185461-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / acetonitrile / 3 h / Ambient temperature

2: 78 percent / H₂ / Pd/C / tetrahydrofuran / 1 h / 760 Torr / Ambient temperature

3: 60 percent / DMAP*CF₃COOH, N,N'-diisopropylcarbodiimide / CHCl₃ / 1.) reflux, 8 h, 2.) room temperature, 16 h

With N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen; benzotriazol-1-ol; 4-N,N-dimethylaminopyridine trifluoroacetate; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; chloroform; acetonitrile;

DOI:10.1021/jo961932h

upstream raw materials:

Boc-(R)-MeLeu-(S)-Thr[Z-(S)-MeTyr(Me)]-(3S,4R,5S)-Ist(TBDMS)-OH

(S)-1-[(S)-2-((S)-4-Hydroxy-2,5-dimethyl-3-oxo-hexanoylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid 2,2,2-trichloro-ethyl ester

1-(tert-butoxycarbonyl)-L-proline

H-Pro-OTce

Downstream raw materials:

Boc-(R)-N(Me)-Leu-Thr[H-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OH

dehydrodidemnin B

cyclo-[N(Me)-O(Me)-Tyr-O-[Boc-(R)-N(Me)-Leu->-Thr-Ist(TBDMS)-Hip-Leu-Pro->

Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OH