8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin

Base Information

• Chemical Name: 8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin
• CAS No.: 216371-68-5
• Molecular Formula: C₅₀H₇₂N₂O₁₅
• Molecular Weight: 941.126

Synonyms:8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin

Chemical Property of 8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin

There total 4 articles about 8-O-(3-[4-{N_α-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin 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: 50.0%

O8-Debutanoylthapsigargin (105662-35-9) + 3-(4-[Nα-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid (216371-80-1) → 8-O-(3-[4-{Nα-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin (216371-68-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 8.5h;

DOI:10.1021/jm010985a

Reference yield:

trans-p-aminocinnamic acid (17570-30-8) → 8-O-(3-[4-{Nα-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin (216371-68-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / 10percent Pd/C / 2-methoxy-ethanol / 3 h / 20 °C / 3040.2 Torr

2.1: SOCl₂ / 20 °C

3.1: PPh₃; hexachloroacetone / tetrahydrofuran / 0.5 h / -78 °C

3.2: 50 percent / pyridine / tetrahydrofuran / 1 h / -78 - 20 °C

4.1: 99 percent / 2M aq. NaOH / methanol / 0.17 h / 20 °C

5.1: 50 percent / DMAP; DCC / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With dmap; sodium hydroxide; thionyl chloride; 1,1,1,3,3,3-hexachloro-propan-2-one; hydrogen; dicyclohexyl-carbodiimide; triphenylphosphine; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol;

DOI:10.1021/jm010985a

Reference yield:

3-(4-aminophenyl)propionic acid (2393-17-1) → 8-O-(3-[4-{Nα-tert-butoxycarbonyl-L-leucinoylamino}phenyl]propanoyl)-8-O-debutanoylthapsigargin (216371-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: SOCl₂ / 20 °C

2.1: PPh₃; hexachloroacetone / tetrahydrofuran / 0.5 h / -78 °C

2.2: 50 percent / pyridine / tetrahydrofuran / 1 h / -78 - 20 °C

3.1: 99 percent / 2M aq. NaOH / methanol / 0.17 h / 20 °C

4.1: 50 percent / DMAP; DCC / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With dmap; sodium hydroxide; thionyl chloride; 1,1,1,3,3,3-hexachloro-propan-2-one; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm010985a

upstream raw materials:

O₈-Debutanoylthapsigargin

3-(4-[N_α-tert-butoxycarbonyl-L-leucinoylamino]phenyl)propanoic acid

3-(4-aminophenyl)propionic acid

trans-p-aminocinnamic acid

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