Piperazinomycin

Base Information

• Chemical Name: Piperazinomycin
• CAS No.: 83858-82-6
• Molecular Formula: C₁₈H₂₀N₂O₂
• Molecular Weight: 296.369
• Mol file: 83858-82-6.mol

Synonyms:13-Oxa-4,20-diazatetracyclo[12.2.2.23,6.18,12]heneicosa-8,10,12(19),14,16,17-hexaen-11-ol,stereoisomer; (+)-Piperazinomycin; Piperazinomycin

Chemical Property of Piperazinomycin

Chemical Property:

• Vapor Pressure: 2.27E-10mmHg at 25°C
• Boiling Point: 493.7°C at 760 mmHg
• Flash Point: 252.4°C
• PSA: 53.52000
• Density: 1.172g/cm³
• LogP: 2.87070

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Piperazinomycin

There total 11 articles about Piperazinomycin 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: 75.0%

C39H38N2O2 (111168-40-2) → (+)-piperazinomycin (83858-82-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; Ambient temperature;

DOI:10.1016/S0040-4039(00)84984-9

Reference yield:

N-formyl-L-tyrosine methyl ester (57085-27-5) → (+)-piperazinomycin (83858-82-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / Br₂, AcONa / 0.58 h / 0 °C

2: 2M HCl / methanol / 0.42 h / Ambient temperature

3: 81 percent / DCC, Et₃N, N-hydroxysuccinimide / dimethylformamide / 22 h / 0 - 25 °C

4: 1.5M HCl / methanol / 1.25 h / Heating

5: 1.) TTN, 2.) zinc powder / 1.) 0-4 deg C, 12 h, then 0 deg C, 3 h; 2.) in AcOH-THF, room temp, 18 h

6: H₂ / 10percent Pd-C-AcONa / methanol / Ambient temperature

7: pyridine / 7 h / Ambient temperature

9: 1.) NaBH₄-BF_3.OEt₂, 2.) 2M aq. HCl, 3.) NaHCO₃ / 1.) in THF, reflux, 17 h; 2.) room temperature, 30 min; 3.) pH 8, room temp., 20 min

10: 75 percent / H₂ / 10 percent Pd-C / methanol / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; boron trifluoride diethyl etherate; hydrogen; bromine; sodium acetate; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; thallium(III) nitrate; zinc; palladium on activated charcoal; Pd-C-AcONa; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84984-9

Reference yield:

N-formyl-3,5-dibromotyrosine methyl ester (107589-78-6) → (+)-piperazinomycin (83858-82-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 2M HCl / methanol / 0.42 h / Ambient temperature

2: 81 percent / DCC, Et₃N, N-hydroxysuccinimide / dimethylformamide / 22 h / 0 - 25 °C

3: 1.5M HCl / methanol / 1.25 h / Heating

4: 1.) TTN, 2.) zinc powder / 1.) 0-4 deg C, 12 h, then 0 deg C, 3 h; 2.) in AcOH-THF, room temp, 18 h

5: H₂ / 10percent Pd-C-AcONa / methanol / Ambient temperature

6: pyridine / 7 h / Ambient temperature

8: 1.) NaBH₄-BF_3.OEt₂, 2.) 2M aq. HCl, 3.) NaHCO₃ / 1.) in THF, reflux, 17 h; 2.) room temperature, 30 min; 3.) pH 8, room temp., 20 min

9: 75 percent / H₂ / 10 percent Pd-C / methanol / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; boron trifluoride diethyl etherate; hydrogen; sodium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; thallium(III) nitrate; zinc; palladium on activated charcoal; Pd-C-AcONa; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84984-9

upstream raw materials:

C₃₉H₃₈N₂O₂

N-formyl-L-tyrosine methyl ester

3,5-dibromotyrosine methyl ester hydrochloride

N-formyl-3,5-dibromotyrosine