22β-(Isobutyryloxy)-3-oxooleana-12-ene-28-oic acid

Base Information

• Chemical Name: 22β-(Isobutyryloxy)-3-oxooleana-12-ene-28-oic acid
• CAS No.: 132194-33-3
• Molecular Formula: C34H52O5
• Molecular Weight: 540.77
• Mol file: 132194-33-3.mol

Synonyms:22β-isobutyryloxy-3-oxo-olean-12-en-28-oic acid;(4R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-4-Isobutyryloxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid;22β-isobutyryloxy-3-oxoolean-12-en-28-oic acid;

Chemical Property of 22β-(Isobutyryloxy)-3-oxooleana-12-ene-28-oic acid

Chemical Property:

• PSA: 80.67000
• LogP: 7.61950

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 22β-(Isobutyryloxy)-3-oxooleana-12-ene-28-oic acid

There total 3 articles about 22β-(Isobutyryloxy)-3-oxooleana-12-ene-28-oic acid 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: 53.1%

diphenylmethyl 22β-isobutyryloxy-3-oxoolean-12-en-28-oate (937736-72-6) → lantadene D (132194-33-3)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; at 20 ℃; for 0.0833333h;

DOI:10.1021/np800167x

Reference yield:

isobutyric acetic anhydride (7137-29-3) + 22β-hydroxy-3-oxo-olean-12-en-28-oic acid (10545-79-6) → lantadene D (132194-33-3)

Guidance literature:

With dmap; In dichloromethane; at 92 - 95 ℃;

DOI:10.1016/j.bmcl.2014.06.068

Reference yield:

22β-angeloyloxy-3-oxo-olean-12-en-28-oic acid (67991-51-9) → lantadene D (132194-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethanol / 6 h / Reflux

2: dmap / dichloromethane / 92 - 95 °C

With dmap; potassium hydroxide; In ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2014.06.068

upstream raw materials:

diphenylmethyl 22β-isobutyryloxy-3-oxoolean-12-en-28-oate

22β-angeloyloxy-3-oxo-olean-12-en-28-oic acid

isobutyric acetic anhydride

22β-hydroxy-3-oxo-olean-12-en-28-oic acid