deacetyllepistine

Base Information

• Chemical Name: deacetyllepistine
• CAS No.: 55623-01-3
• Molecular Formula: C₈H₁₄N₂O
• Molecular Weight: 154.212
• Mol file: 55623-01-3.mol

Synonyms:

Chemical Property of deacetyllepistine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of deacetyllepistine

There total 8 articles about deacetyllepistine 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: 12.0%

(R)-3,9-bis(2-nitrobenzenesulfonyl)-11-oxa-3,9-diazabicyclo[5.3.1]undec-7-ene (1609184-10-2) → deacetyllepistine (55623-01-3)

Guidance literature:

With caesium carbonate; thiophenol; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol5010033

Reference yield:

5-((tert-butyldimethylsilyl)oxy)-2-methylenepentan-1-ol (1071056-81-9) → deacetyllepistine (55623-01-3)

Guidance literature:

Multi-step reaction with 8 steps

1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.67 h / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 9 h / 20 °C / Inert atmosphere

3: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

4: HSiPh₃; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 2 h / 20 °C / Inert atmosphere

5: caesium carbonate / acetonitrile / 24 h / 80 °C / Inert atmosphere

6: ozone; dimethylsulfide / dichloromethane; methanol / -78 - 20 °C / Inert atmosphere

7: camphor-10-sulfonic acid / m-xylene / 0.33 h / Reflux; Inert atmosphere

8: caesium carbonate; thiophenol / acetonitrile / 1 h / 20 °C / Inert atmosphere

With azodicarboxylic acid bis(2-methoxyethyl) ester; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; caesium carbonate; ozone; acetic acid; thiophenol; triphenylphosphine; diethylazodicarboxylate; HSiPh₃; In tetrahydrofuran; methanol; dichloromethane; m-xylene; toluene; acetonitrile; 1: |Mitsunobu Displacement;

DOI:10.1021/ol5010033

Reference yield:

(S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide (1609184-04-4) → deacetyllepistine (55623-01-3)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 9 h / 20 °C / Inert atmosphere

2: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

3: HSiPh₃; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 2 h / 20 °C / Inert atmosphere

4: caesium carbonate / acetonitrile / 24 h / 80 °C / Inert atmosphere

5: ozone; dimethylsulfide / dichloromethane; methanol / -78 - 20 °C / Inert atmosphere

6: camphor-10-sulfonic acid / m-xylene / 0.33 h / Reflux; Inert atmosphere

7: caesium carbonate; thiophenol / acetonitrile / 1 h / 20 °C / Inert atmosphere

With azodicarboxylic acid bis(2-methoxyethyl) ester; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; caesium carbonate; ozone; acetic acid; thiophenol; triphenylphosphine; HSiPh₃; In tetrahydrofuran; methanol; dichloromethane; m-xylene; acetonitrile;

DOI:10.1021/ol5010033

upstream raw materials:

5-((tert-butyldimethylsilyl)oxy)-2-methylenepentan-1-ol

(S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

(S)-N-glycidyl-N-(5-hydroxy-2-methylenepentyl)-2-nitrobenzenesulfonamide

(S)-N-(5-(N-allyloxycarbonyl-2-nitrobenzenesulfonamido)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide