(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

Base Information

• Chemical Name: (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
• CAS No.: 86527-45-9
• Molecular Formula: C₃₅H₅₃NO₄Si
• Molecular Weight: 579.896

Synonyms:(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

Chemical Property of (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

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)-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 2 articles about (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 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:

(E)-(1R,6R,10S,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) → (E)-(1R,6R,10S,14R,17R,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-45-9) + (E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-45-9)

Guidance literature:

With potassium carbonate; In methanol; Yield given. Yields of byproduct given;

DOI:10.1021/ja00354a072

Reference yield:

(E)-(1R,6R,10S,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) → (E)-(1R,6R,10S,14R,17R,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-45-9) + (E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-45-9)

Guidance literature:

With potassium carbonate; In methanol; Yield given. Yields of byproduct given;

DOI:10.1021/ja00354a072

Reference yield:

(E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione (86527-45-9) → cytochalasin B (14930-96-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C

2: H₂O₂ / pyridine; CH₂Cl₂

3: 88 percent / DMAP / triethylamine

4: 89 percent Turnov_. / t-BuOOH/Mo(CO)6 / benzene / 1.5 h / 75 °C

With tert.-butylhydroperoxide; dmap; hexacarbonyl molybdenum; dihydrogen peroxide; lithium diisopropyl amide; In pyridine; dichloromethane; triethylamine; benzene;

DOI:10.1021/ja00354a072

upstream raw materials:

(E)-(1R,6R,10S,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

Downstream raw materials:

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

(4E,12E)-(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-4,12,15-triene-3,21-dione

C₃₇H₅₃NO₆Si

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