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

Base Information

• Chemical Name: Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OH
• CAS No.: 185461-54-5
• Molecular Formula: C₆₈H₁₀₈N₆O₁₇Si
• Molecular Weight: 1309.72
• Mol file: 185461-54-5.mol

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

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

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-OH

There total 20 articles about Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OH 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: 81.0%

Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OTce (185461-53-4) → Boc-(R)-N(Me)-Leu-Thr[Z-N(Me)-O(Me)-Tyr]-Ist(TBDMS)-Hip-Leu-Pro-OH (185461-54-5)

Guidance literature:

With ammonium acetate; zinc; In tetrahydrofuran; for 24h;

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-OH (185461-54-5)

Guidance literature:

Multi-step reaction with 6 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

6: 81 percent / aq. NH₄OAc, Zn / tetrahydrofuran / 24 h

With dmap; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; ammonium acetate; hydrogen; benzotriazol-1-ol; 4-N,N-dimethylaminopyridine trifluoroacetate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; diisopropyl-carbodiimide; zinc; 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-OH (185461-54-5)

Guidance literature:

Multi-step reaction with 4 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

4: 81 percent / aq. NH₄OAc, Zn / tetrahydrofuran / 24 h

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

DOI:10.1021/jo961932h

upstream raw materials:

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

1-(tert-butoxycarbonyl)-L-proline

H-Pro-OTce

(2S)-3-[4-(methyloxy)phenyl]-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid

Downstream raw materials:

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

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

dehydrodidemnin B