8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin

Base Information

• Chemical Name: 8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin
• CAS No.: 391610-97-2
• Molecular Formula: C₅₆H₈₄N₂O₁₅
• Molecular Weight: 1025.29

Synonyms:8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin

Chemical Property of 8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin

Chemical Property:

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Technology Process of 8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin

There total 4 articles about 8-O-(12-[N_α-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-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: 73.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 8-O-(12-aminododecanoyl)-8-O-debutanoylthapsigargin (380225-59-2) → 8-O-(12-[Nα-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin (391610-97-2)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/jm010985a

Reference yield:

O8-Debutanoylthapsigargin (105662-35-9) → 8-O-(12-[Nα-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin (391610-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 - 20 °C

2: 100 percent / TFA / CH₂Cl₂ / 0.75 h / 20 °C

3: 73 percent / DCC; HOBT / dimethylformamide / 4.5 h / 0 - 20 °C

With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm010985a

Reference yield:

12-Aminododecanoic acid (693-57-2) → 8-O-(12-[Nα-tert-butoxycarbonyl-L-phenylalaninoylamino]dodecanoyl)-8-O-debutanoylthapsigargin (391610-97-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / 5M aq. NaOH / 2-methyl-propan-2-ol / 20 °C

2: 77 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 - 20 °C

3: 100 percent / TFA / CH₂Cl₂ / 0.75 h / 20 °C

4: 73 percent / DCC; HOBT / dimethylformamide / 4.5 h / 0 - 20 °C

With dmap; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm010985a

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

8-O-(12-aminododecanoyl)-8-O-debutanoylthapsigargin

O₈-Debutanoylthapsigargin

12-Aminododecanoic acid

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