(3beta)-3-Hydroxy-2-(hydroxyimino)olean-12-en-28-oic acid phenylmethyl ester

Base Information

• Chemical Name: (3beta)-3-Hydroxy-2-(hydroxyimino)olean-12-en-28-oic acid phenylmethyl ester
• CAS No.: 892869-55-5
• Molecular Formula: C37H53 N O4
• Molecular Weight: 575.82
• Mol file: 892869-55-5.mol

Synonyms:(3β)-3-Hydroxy-2- (hydroxyimino)- olean- 12-en-28-oic acid phenylmethyl ester;(3BETA)-3-HYDROXY-2-(HYDROXYIMINO)OLEAN-12-EN-28-OIC ACID PHENYLMETHYL ESTER

Chemical Property of (3beta)-3-Hydroxy-2-(hydroxyimino)olean-12-en-28-oic acid phenylmethyl ester

Chemical Property:

• Refractive Index: 1.602
• PSA: 79.12000
• LogP: 8.33250

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3beta)-3-Hydroxy-2-(hydroxyimino)olean-12-en-28-oic acid phenylmethyl ester

There total 5 articles about (3beta)-3-Hydroxy-2-(hydroxyimino)olean-12-en-28-oic acid phenylmethyl ester 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: 78.0%

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-[(E)-Hydroxyimino]-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 (892869-52-2) → (4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-Hydroxy-11-[(E)-hydroxyimino]-2,2,6a,6b,9,9,12a-heptamethyl-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 (892869-55-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃;

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) → (4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-Hydroxy-11-[(E)-hydroxyimino]-2,2,6a,6b,9,9,12a-heptamethyl-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 (892869-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / NaNO₂; aq. H₂SO₄ / methanol; tetrahydrofuran / 20 °C

2: 78 percent / NaBH₄ / tetrahydrofuran / 0 °C

With sodium tetrahydroborate; sulfuric acid; sodium nitrite; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2006.03.009

Reference yield:

Oleanolic acid (508-02-1) → (4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-Hydroxy-11-[(E)-hydroxyimino]-2,2,6a,6b,9,9,12a-heptamethyl-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 (892869-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / K₂CO₃ / dimethylformamide / 60 °C

2: 89 percent / PCC / CH₂Cl₂ / 20 °C

3: 58 percent / NaNO₂; aq. H₂SO₄ / methanol; tetrahydrofuran / 20 °C

4: 78 percent / NaBH₄ / tetrahydrofuran / 0 °C

With sodium tetrahydroborate; sulfuric acid; potassium carbonate; pyridinium chlorochromate; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.03.009

upstream raw materials:

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-[(E)-Hydroxyimino]-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

(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

Oleanolic acid

benzyl chloride

Refernces