Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid

Base Information

• Chemical Name: Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid
• CAS No.: 218600-48-7
• Molecular Formula: C31H45 N O3
• Molecular Weight: 479.69
• Mol file: 218600-48-7.mol

Synonyms:Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid

Chemical Property of Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid

Chemical Property:

• PSA: 63.33000
• LogP: 7.57460

Purity/Quality:

98%Min ^*data from raw suppliers

OLEANA-2,12-DIENO[2,3-D]ISOXAZOL-28-OIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid

There total 9 articles about Oleana-2,12-dieno[2,3-d]isoxazol-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: 99.0%

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-Formyl-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 (218600-47-6) → isoxazolo[4,5-b]olean-12-en-28-oic acid (218600-48-7)

Guidance literature:

With hydroxylamine hydrochloride; In ethanol;

DOI:10.1016/S0960-894X(98)00479-X

Reference yield: 12.0%

C38H51NO3 (892869-60-2) → isoxazolo[4,5-b]olean-12-en-28-oic acid (218600-48-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2006.03.009

Reference yield:

(4aS,6aS,6bR,12aR)-benzyl 2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate (869788-74-9) → isoxazolo[4,5-b]olean-12-en-28-oic acid (218600-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaOMe / CH₂Cl₂ / 20 °C

2: 95 percent / hydroxylamine hydrochloride / aq. ethanol / 2 h / 80 °C

3: 12 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

With hydroxylamine hydrochloride; hydrogen; sodium methylate; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.bmcl.2006.03.009

upstream raw materials:

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-Formyl-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

C₃₈H₅₁NO₃

(4aS,6aS,6bR,12aR)-benzyl 2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-[1-Hydroxy-meth-(Z)-ylidene]-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 benzyl ester

Refernces

• 1、 Wu, Jing,Bao, Bei-Hua,Shen, Qi,Zhang, Yu-Chao,Jiang, Qing,Li, Jian-Xin. "Novel heterocyclic ring-fused oleanolic acid derivatives as osteoclast inhibitors for osteoporosis". . p. 371 - 377. Retrieved 2016/03/01.
• 2、 Chen, Jun,Liu, Jun,Zhang, Luyong,Wu, Guanzhong,Hua, Weiyi,Wu, Xiaoming,Sun, Hongbin. "Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase". . p. 2915 - 2919. Retrieved 2007/10/03.