(E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

Base Information

• Chemical Name: (E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione
• CAS No.: 86527-61-9
• Molecular Formula: C₃₇H₅₅NO₅Si
• Molecular Weight: 621.933

Synonyms:

Chemical Property of (E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

There total 34 articles about (E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-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:

(3R)-citronellol (1117-61-9) → (E)-(1R,6R,10S,14R,17R,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-61-9,86562-59-6)

Guidance literature:

Multi-step reaction with 14 steps

1: NaH / tetrahydrofuran

2: 85 percent / OsO₄/N-methylmorpholine N-oxide, H₅IO₆

4: H₂O

5: LiAlH₄/(-)-N-methylephedrine / diethyl ether / -15 °C

7: 1.) RLi / 2.) THF, -78 deg C

8: H₂ / 5percent Rh/Al₂O₃ / ethanol

9: H₂ / 10percent Pd/C / ethanol

10: 80 percent / pyridinium chlorochromate

11: 69 percent / 1.) RLi / 2.) THF, -78 deg C; HMPA, RT, 3 h

12: NaOH / aq. ethanol

13: 69 percent / 2-chloropyridine methiodide, DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

14: 1,3,5-trimethyl-benzene / 144 h / 180 - 190 °C

With dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; (-)-N-methylephedrine; water; hydrogen; sodium hydride; 4-methylmorpholine N-oxide; periodic acid; triethylamine; pyridinium chlorochromate; 2-chloropyridinium methiodide; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1,3,5-trimethyl-benzene;

DOI:10.1021/ja00354a072

Reference yield:

(3R)-citronellol (1117-61-9) → (E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-61-9,86562-59-6)

Guidance literature:

Multi-step reaction with 14 steps

1: NaH / tetrahydrofuran

2: 85 percent / OsO₄/N-methylmorpholine N-oxide, H₅IO₆

4: H₂O

5: LiAlH₄/(-)-N-methylephedrine / diethyl ether / -15 °C

7: 1.) RLi / 2.) THF, -78 deg C

8: H₂ / 5percent Rh/Al₂O₃ / ethanol

9: H₂ / 10percent Pd/C / ethanol

10: 80 percent / pyridinium chlorochromate

11: 69 percent / 1.) RLi / 2.) THF, -78 deg C; HMPA, RT, 3 h

12: NaOH / aq. ethanol

13: 69 percent / 2-chloropyridine methiodide, DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

14: 1,3,5-trimethyl-benzene / 144 h / 180 - 190 °C

With dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; (-)-N-methylephedrine; water; hydrogen; sodium hydride; 4-methylmorpholine N-oxide; periodic acid; triethylamine; pyridinium chlorochromate; 2-chloropyridinium methiodide; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1,3,5-trimethyl-benzene;

DOI:10.1021/ja00354a072

Reference yield:

(R)-(+)-citronellyl benzyl ether (83541-12-2) → (E)-(1R,6R,10S,14R,17R,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-61-9,86562-59-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 85 percent / OsO₄/N-methylmorpholine N-oxide, H₅IO₆

3: H₂O

4: LiAlH₄/(-)-N-methylephedrine / diethyl ether / -15 °C

6: 1.) RLi / 2.) THF, -78 deg C

7: H₂ / 5percent Rh/Al₂O₃ / ethanol

8: H₂ / 10percent Pd/C / ethanol

9: 80 percent / pyridinium chlorochromate

10: 69 percent / 1.) RLi / 2.) THF, -78 deg C; HMPA, RT, 3 h

11: NaOH / aq. ethanol

12: 69 percent / 2-chloropyridine methiodide, DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

13: 1,3,5-trimethyl-benzene / 144 h / 180 - 190 °C

With dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; (-)-N-methylephedrine; water; hydrogen; 4-methylmorpholine N-oxide; periodic acid; triethylamine; pyridinium chlorochromate; 2-chloropyridinium methiodide; palladium on activated charcoal; Rh/Al₂O₃; In diethyl ether; ethanol; dichloromethane; 1,3,5-trimethyl-benzene;

DOI:10.1021/ja00354a072

upstream raw materials:

(10E,12E,14E)-(4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8,14-dimethyl-hexadeca-10,12,14-trienoic acid (S)-1-acetyl-5-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl ester

(3R)-citronellol

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

(R)-(+)-citronellyl benzyl ether

Downstream raw materials:

(E)-(1R,6R,10S,14R,17R,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

(E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

cytochalasin F

(4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione

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