benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate

Base Information

• Chemical Name: benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate
• CAS No.: 1256959-23-5
• Molecular Formula: C₄₁H₅₇NO₆
• Molecular Weight: 659.907
• Mol file: 1256959-23-5.mol

Synonyms:benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate

Chemical Property of benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate

There total 4 articles about benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate 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:

benzyl 3-hydroxyimino-lup-20(29)-en-28-oate (1256959-22-4) + acetic anhydride (108-24-7) → benzyl 3-acetoxyimino-23-acetoxy-lup-20(29)-en-28-oate (1256959-23-5)

Guidance literature:

benzyl 3-hydroxyimino-lup-20⁽²⁹⁾-en-28-oate; With sodium tetrachloropalladate(II); sodium acetate; acetic acid; at 20 ℃; for 72h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

With pyridine; lead(IV) tetraacetate; acetic acid; In tetrahydrofuran; at -78 - 20 ℃; for 20h;

DOI:10.3184/174751912X13332875186150

Reference yield:

benzyl bromide (100-39-0) → benzyl 3-acetoxyimino-23-acetoxy-lup-20(29)-en-28-oate (1256959-23-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

2.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C

3.1: pyridine; hydroxylamine hydrochloride / 4 h / 80 °C

4.1: sodium tetrachloropalladate(II); sodium acetate; acetic acid / 72 h / 20 °C

4.2: 1 h / 20 °C

4.3: 20 h / -78 - 20 °C

With pyridine; sodium tetrachloropalladate(II); hydroxylamine hydrochloride; sodium acetate; potassium carbonate; acetic acid; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.3184/174751912X13332875186150

Reference yield:

benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate (192211-42-0) → benzyl 3-acetoxyimino-23-acetoxy-lup-20(29)-en-28-oate (1256959-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C

2.1: pyridine; hydroxylamine hydrochloride / 4 h / 80 °C

3.1: sodium tetrachloropalladate(II); sodium acetate; acetic acid / 72 h / 20 °C

3.2: 1 h / 20 °C

3.3: 20 h / -78 - 20 °C

With pyridine; sodium tetrachloropalladate(II); hydroxylamine hydrochloride; sodium acetate; acetic acid; pyridinium chlorochromate; In dichloromethane;

DOI:10.3184/174751912X13332875186150

upstream raw materials:

benzyl 3-hydroxyimino-lup-20⁽²⁹⁾-en-28-oate

acetic anhydride

benzyl bromide

benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

Downstream raw materials:

benzyl 3-hydroxyimino-23-hydroxy-lup-20⁽²⁹⁾-en-28-oate

benzyl 3-oxo-23-hydroxy-lup-20⁽²⁹⁾-en-28-oate

23-hydroxybetulinic acid