C₂₉H₄₄BrN₅O₁₀S

Base Information

• Chemical Name: C₂₉H₄₄BrN₅O₁₀S
• CAS No.: 918906-33-9
• Molecular Formula: C₂₉H₄₄BrN₅O₁₀S
• Molecular Weight: 734.666
• Mol file: 918906-33-9.mol

Synonyms:C₂₉H₄₄BrN₅O₁₀S

Chemical Property of C₂₉H₄₄BrN₅O₁₀S

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₉H₄₄BrN₅O₁₀S

There total 10 articles about C₂₉H₄₄BrN₅O₁₀S 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: 51.0%

Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu (918906-32-8) + phosgene (75-44-5) + N-(4-bromophenyl)hydroxylamine (10468-46-9) → C29H44BrN5O10S (918906-33-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2006.08.121

Reference yield:

N-tert-butyloxycarbonylasparagine (7536-55-2) → C29H44BrN5O10S (918906-33-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 67 percent / iodosobenzene diacetate / ethyl acetate; acetonitrile; H₂O

2: 94 percent / KOH; K₂CO₃ / tetrahydrofuran; H₂O

3: 84 percent / DCC; DMAP / CH₂Cl₂

4: 94 percent / H₂ / Pd/C / methanol

5: 67 percent / N-methylmorpholine / CH₂Cl₂

6: 80 percent / (PPh₃)4Pd; morpholine / CH₂Cl₂

7: 78 percent / EDC; HOBt; N-methylmorpholine / CH₂Cl₂

8: 94 percent / tributhylphosphine / tetrahydrofuran; H₂O

9: 51 percent / DIPEA / CH₂Cl₂ / 0 - 20 °C

With morpholine; 4-methyl-morpholine; dmap; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributylphosphine; [bis(acetoxy)iodo]benzene; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 1: Hofmann reaction;

DOI:10.1016/j.bmcl.2006.08.121

Reference yield:

(S)-3-amino-2-tert-butoxycarbonylaminopropionic acid (76387-70-7) → C29H44BrN5O10S (918906-33-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / KOH; K₂CO₃ / tetrahydrofuran; H₂O

2: 84 percent / DCC; DMAP / CH₂Cl₂

3: 94 percent / H₂ / Pd/C / methanol

4: 67 percent / N-methylmorpholine / CH₂Cl₂

5: 80 percent / (PPh₃)4Pd; morpholine / CH₂Cl₂

6: 78 percent / EDC; HOBt; N-methylmorpholine / CH₂Cl₂

7: 94 percent / tributhylphosphine / tetrahydrofuran; H₂O

8: 51 percent / DIPEA / CH₂Cl₂ / 0 - 20 °C

With morpholine; 4-methyl-morpholine; dmap; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributylphosphine; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmcl.2006.08.121

upstream raw materials:

Boc-γ-Gla[-Cys(SH)-Gly-OtBu]-OtBu

phosgene

N-(4-bromophenyl)hydroxylamine

Boc-γ-Gla[-Cys(StBu)-OH]-OtBu

Refernces