(16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione

Base Information

• Chemical Name: (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione
• CAS No.: 122749-14-8
• Molecular Formula: C₄₃H₄₂N₂O₅
• Molecular Weight: 666.817

Synonyms:(16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione

Chemical Property of (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione

Chemical Property:

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Technology Process of (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione

There total 21 articles about (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione 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: 71.0%

(16S)-2-benzoyl-10-(1-benzoylindol-3-yl)-18,18-ethylenedioxy-16-methyl<11>cytochalasa-6(7),13t-diene-1,21-dione (109355-86-4) → (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13t-diene-1,18,21-trione (122749-14-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 24h; Ambient temperature;

Reference yield:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13t-diene-1,18,21-trione (122749-14-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / i-Bu₂AlH

2: 70 percent / LDA

3: 81 percent / H₂, AcOH / Pd/C / ethanol

4: 95 percent / NaOEt / ethanol

5: 77 percent / Et₃N, DMAP

6: 68 percent / LiN(SiMe₃)2

7: 84 percent / LiN(SiMe₃)2

8: H₂O₂, m-chloroperoxybenzoic acid / 1.) -40 deg C, 2.) 0 deg C

9: toluene / 7 h / 80 °C

10: 71 percent / 5percent aq. HCl / tetrahydrofuran

With hydrogenchloride; dmap; hydrogen; dihydrogen peroxide; sodium ethanolate; diisobutylaluminium hydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;

DOI:10.1039/c39860001447

Reference yield:

(E)-(S)-4-Benzyloxycarbonylamino-5-(1H-indol-3-yl)-pent-2-enoic acid ethyl ester (109374-23-4) → (16S)-2-benzoyl-10-(N-benzoylindol-3-yl)-16-methyl<11>cytochalasa-6(7),13t-diene-1,18,21-trione (122749-14-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / H₂, AcOH / Pd/C / ethanol

2: 95 percent / NaOEt / ethanol

3: 77 percent / Et₃N, DMAP

4: 68 percent / LiN(SiMe₃)2

5: 84 percent / LiN(SiMe₃)2

6: H₂O₂, m-chloroperoxybenzoic acid / 1.) -40 deg C, 2.) 0 deg C

7: toluene / 7 h / 80 °C

8: 71 percent / 5percent aq. HCl / tetrahydrofuran

With hydrogenchloride; dmap; hydrogen; dihydrogen peroxide; sodium ethanolate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;

DOI:10.1039/c39860001447

upstream raw materials:

(16S)-2-benzoyl-10-(1-benzoylindol-3-yl)-18,18-ethylenedioxy-16-methyl<11>cytochalasa-6(7),13^t-diene-1,21-dione

(S)-Citronellal

(2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester

(6S)-ethyl 6,10-dimethyl-4-oxoundec-9-enoate

Downstream raw materials:

cytochalasin G

(6R,7S,16S)-2-benzoyl-10-(1-benzoylindol-3-yl)-6,7-epoxy-16-methyl<11>cytochalas-13^t-ene-1,18,21-trione

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