(7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione

Base Information

• Chemical Name: (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione
• CAS No.: 129063-36-1
• Molecular Formula: C₄₁H₅₃NO₄Si
• Molecular Weight: 651.962

Synonyms:(7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione

Chemical Property of (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione

There total 12 articles about (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,17-triene-1,21-dione 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: 85.0%

(6R,7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-6-hydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-13,17-diene-1,21-dione (129056-36-6) → (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,17-triene-1,21-dione (129063-36-1)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1039/a906412e

Reference yield: 75.0%

(5E,9E)-(1R,7S,11R,12S,14S,15R,16S)-17-Benzoyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-13-hydroxy-5,7,13,14-tetramethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-5,9-diene-2,18-dione (129056-36-6) → (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,17-triene-1,21-dione (129063-36-1)

Guidance literature:

With thionyl chloride; triethylamine;

DOI:10.1039/c39900000464

Reference yield:

(5R)-1-benzoyl-5-benzylpyrrolidin-2-one (94063-58-8) → (7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,17-triene-1,21-dione (129063-36-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiN(SiMe₃)2 / tetrahydrofuran; hexane / 1 h / -70 °C

1.2: 92 percent / tetrahydrofuran / 4 h / -70 - 20 °C

2.1: LiN(SiMe₃)2 / tetrahydrofuran; hexane / 1 h / -70 °C

2.2: 100 percent / tetrahydrofuran; hexane / 2 h / -70 °C

3.1: H₂O₂; MCPBA / H₂O; CHCl₃ / 0.33 h / -50 - 0 °C

4.1: benzene / 8 h / Heating

5.1: 53 percent / OsO₄ / pyridine / 1 h / -15 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

7.1: 85 percent / NEt₃; SOCl₂ / CH₂Cl₂ / 0.5 h / -20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; thionyl chloride; dihydrogen peroxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; hexane; dichloromethane; chloroform; water; benzene; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Phenylselenenylation / 3.1: Oxidation / 4.1: Cycloaddition / 5.1: Oxidation / 6.1: Etherification / 7.1: Dehydration;

DOI:10.1039/a906412e

upstream raw materials:

(5E,9E)-(1R,7S,11R,12S,14S,15R,16S)-17-Benzoyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-13-hydroxy-5,7,13,14-tetramethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-5,9-diene-2,18-dione

(6R,7S,13E,16S,17E)-2-Benzoyl-7-tert-butyldimethylsilyloxy-6-hydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-13,17-diene-1,21-dione

t-butyldimethylsiyl triflate

(5R)-1-benzoyl-5-benzylpyrrolidin-2-one

Downstream raw materials:

cytochalasin D

C₅₀H₆₃NO₆SeSi

C₄₃H₅₉NO₅SeSi

C₃₇H₅₅NO₅Si

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