(7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one

Base Information

• Chemical Name: (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one
• CAS No.: 104702-08-1
• Molecular Formula: C₃₆H₅₃NO₆Si
• Molecular Weight: 623.905
• Mol file: 104702-08-1.mol

Synonyms:(7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one

Chemical Property of (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one

There total 30 articles about (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one 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%

(6R,7S,16S,18R,21R)-21-acetoxy-6,7-epoxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-13t,19t-dien-1-one (104702-07-0) → (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13t,19t-trien-1-one (104702-08-1)

Guidance literature:

With aluminum isopropoxide; In o-xylene; at 125 ℃; for 5h;

Reference yield: 65.0%

(6R,7S,16S,18R,21R)-21-acetoxy-6,7-epoxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-13t,19t-dien-1-one (104702-07-0) → (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13t,19t-trien-1-one (104702-08-1) + Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,15R,16S)-16-benzyl-12-hydroxy-5,7,13,14-tetramethyl-18-oxo-5-(2-trimethylsilanyl-ethoxymethoxy)-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9,13-trien-2-yl ester

Guidance literature:

With aluminum isopropoxide; In xylene; at 125 ℃;

DOI:10.1039/c39860000727

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13t,19t-trien-1-one (104702-08-1)

Guidance literature:

Multi-step reaction with 22 steps

1: 86 percent / ethyl di-isopropylamine / CH₂Cl₂ / 2 h / Heating

2: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature

3: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr

4: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) -60 deg C, 15 min

5: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C

6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min

7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min

8: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h

9: 98 percent / sodium hydroxide / methanol; H₂O / 3 h / Ambient temperature

10: 95 percent / tetrahydrofuran / 12 h

11: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C

12: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C

13: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl₃ / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min

14: 37 percent / toluene / 5 h / 100 °C

15: 98 percent / sodium hydroxide / H₂O; methanol / 2 h / 0 °C

16: 98 percent / lithium di-isopropylamide / tetrahydrofuran; hexane / 2 h

17: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

18: 68 percent / pyridine, 30percent aq. hydrogen peroxide / CH₂Cl₂ / 12 h / Ambient temperature

19: 72 percent / sodium borohydride / ethanol / 3 h / 0 °C

20: 94 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

21: 19 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h

22: 67 percent / aluminium isopropoxide / o-xylene / 5 h / 125 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; Dowex 50W X-8; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; aluminum isopropoxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform-d1; ethanol; hexane; dichloromethane; o-xylene; water; toluene;

upstream raw materials:

(6R,7S,16S,18R,21R)-21-acetoxy-6,7-epoxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-13^t,19^t-dien-1-one

(16S,18R)-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(7),13^t,19^t-triene-1,21-dione

(16S,18R,21R)-21-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(7),13^t,19^t-trien-1-one

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

Downstream raw materials:

cytochalasin H