(7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,21-dione

Base Information

• Chemical Name: (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,21-dione
• CAS No.: 129056-41-3
• Molecular Formula: C₃₇H₅₃NO₅Si
• Molecular Weight: 619.917

Synonyms:(7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,21-dione

Chemical Property of (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,21-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,21-dione

There total 19 articles about (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-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: 67.0%

C43H59NO5SeSi (129056-40-2) → (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,21-dione (129056-41-3)

Guidance literature:

With dihydrogen peroxide; In pyridine; water;

DOI:10.1039/c39900000464

Reference yield: 65.0%

(7S,13E,16S,17R,18R,20R)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl-20-phenylseleno[11]cytochalasa-6(12),13-diene-1,21-dione (259139-94-1) → (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,21-dione (129056-41-3)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; water; at 20 ℃; for 3h;

DOI:10.1039/a906412e

Reference yield:

(S)-1-Benzoyl-5-benzyl-3-((4E,8E,10E,12E)-(S)-4,6,12-trimethyl-tetradeca-4,8,10,12-tetraenoyl)-1,5-dihydro-pyrrol-2-one (129063-34-9) → (7S,13E,16S,17R,18R,19E)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,21-dione (129056-41-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: benzene / 8 h / Heating

2.1: 53 percent / OsO₄ / pyridine / 1 h / -15 °C

3.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 85 percent / NEt₃; SOCl₂ / CH₂Cl₂ / 0.5 h / -20 °C

5.1: 75 percent / OsO₄ / pyridine / 0.5 h / -25 °C

6.1: 99 percent / p-TsOH / CHCl₃ / 5 h / 20 °C

7.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -35 °C

7.2: 70 percent / tetrahydrofuran / 1.5 h / -35 °C

8.1: 97 percent / NaOH; H₂O / methanol / 3 h / 20 °C

9.1: 65 percent / H₂O₂; pyridine / CH₂Cl₂; H₂O / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; osmium(VIII) oxide; thionyl chloride; water; dihydrogen peroxide; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; benzene; 1.1: Cycloaddition / 2.1: Oxidation / 3.1: Etherification / 4.1: Dehydration / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Phenylselenenylation / 8.1: Hydrolysis / 9.1: Elimination;

DOI:10.1039/a906412e

upstream raw materials:

C₄₃H₅₉NO₅SeSi

(7S,13E,16S,17R,18R,20R)-7-tert-Butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl-20-phenylseleno[11]cytochalasa-6⁽¹²⁾,13-diene-1,21-dione

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(7S,13E,16S,17R,18R,19E,21R)-7-tert-Butyldimethylsilyloxy-21-hydroxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1-one

C₃₇H₅₅NO₅Si

cytochalasin D

(7S,13E,16S,17R,18R,19E,21R)-21-Acetoxy-7-hydroxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1-one

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