(16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,21-dione

Base Information

• Chemical Name: (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,21-dione
• CAS No.: 104702-00-3
• Molecular Formula: C₂₈H₃₇NO₃
• Molecular Weight: 435.607

Synonyms:(16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,21-dione

Chemical Property of (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,21-dione

Chemical Property:

Purity/Quality:

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Technology Process of (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,21-dione

There total 40 articles about (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-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: 84.0%

methylmagnesium chloride (676-58-4) + (16S)-16-methyl-10-phenyl<11>cytochalasa-6(7),13t-diene-1,18,21-trione (109466-58-2) → (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13t-diene-1,21-dione (104702-00-3)

Guidance literature:

In tetrahydrofuran; 1.) 5 min, 0 deg C, 2.) 3 h, room temperature;

Reference yield: 75.0%

(16S,18S)-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(7),13t-diene-1,21-dione (104720-31-2) → (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13t-diene-1,21-dione (104702-00-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1039/c39860000724

Reference yield:

(2R,4R)-5-(dimethyl-t-butylsiloxy)-2-hydroxy-2,4-dimethylpentanal (104701-90-8) → (16S,18S)-18-hydroxy-16,18-dimethyl-10-phenyl<11>cytochalasa-6(7),13t-diene-1,21-dione (104702-00-3)

Guidance literature:

Multi-step reaction with 17 steps

1: 70 percent

2: 85 percent / Et₂N-i-Pr

3: 70 percent / Dowex 50W-X₈

4: 95 percent / H₂ / Pd/C / methanol

5: 90 percent / DMSO, oxalyl chloride

6: 70 percent

7: 1.) 9-BBN, 2.) H₂O₂, base

8: 90 percent / DMSO, oxalyl chloride

10: 90 percent / NaOH / methanol; H₂O

11: 90 percent

12: LiN(SiMe₃)2

13: 95 percent / LiN(SiMe₃)2

14: MCPBA, H₂O₂ / 1.) -40 deg C, 15 min, 2.) 0 deg C

15: toluene / 5 h / 80 - 100 °C

16: 85 percent / KOH / methanol

17: 75 percent / 5percent aq. HF / acetonitrile

With potassium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; N,N-diethyl-N-isopropylamine; Dowex 50W-X₈; hydrogen fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In methanol; water; toluene; acetonitrile;

DOI:10.1039/c39860000724

upstream raw materials:

methylmagnesium chloride

(16S)-16-methyl-10-phenyl<11>cytochalasa-6(7),13^t-diene-1,18,21-trione

(16S,18S)-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(7),13^t-diene-1,21-dione

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

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