methyl 23-benzyloxy-3-oxours-12-en-28-oate

Base Information

• Chemical Name: methyl 23-benzyloxy-3-oxours-12-en-28-oate
• CAS No.: 303174-78-9
• Molecular Formula: C₃₈H₅₄O₄
• Molecular Weight: 574.844
• Mol file: 303174-78-9.mol

Synonyms:methyl 23-benzyloxy-3-oxours-12-en-28-oate

Chemical Property of methyl 23-benzyloxy-3-oxours-12-en-28-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 23-benzyloxy-3-oxours-12-en-28-oate

There total 9 articles about methyl 23-benzyloxy-3-oxours-12-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: 91.0%

methyl 23-benzyloxy-3,3-ethylenedioxyurs-12-en-28-oate (303174-77-8) → methyl 23-benzyloxy-3-oxours-12-en-28-oate (303174-78-9)

Guidance literature:

With pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In acetone; at 20 ℃; for 48h;

DOI:10.1021/jo0008688

Reference yield:

ursolic acid (77-52-1) → methyl 23-benzyloxy-3-oxours-12-en-28-oate (303174-78-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diethyl ether; tetrahydrofuran

2.1: Jones / acetone

3.1: NH₂OH*HCl; NaOAc / methanol; CH₂Cl₂

4.1: Na₂PdCl₄; NaOAc / acetic acid / 72 h

4.2: DMAP; Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

4.3: 1.92 g / Pb(OAc)4 / pyridine; tetrahydrofuran; acetic acid / 16 h / 20 °C

5.1: 98 percent / Na₂CO₃ / methanol / 16 h / 20 °C

6.1: 88 percent / 20percent HCl; NH₄OAc / TiCl₃ / H₂O; tetrahydrofuran / 4 h / 20 °C

7.1: 99 percent / PPTS; MS / benzene / 20 h / Heating

8.1: 94 percent / KH; n-Bu₄NI / tetrahydrofuran / 28 h / Heating

9.1: 91 percent / p-TsOH; PPTS / acetone / 48 h / 20 °C

With sodium tetrachloropalladate(II); hydroxylamine hydrochloride; ammonium acetate; sodium acetate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium carbonate; toluene-4-sulfonic acid; titanium(III) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetone; benzene; 1.1: Methylation / 2.1: Oxidation / 3.1: oximation / 4.1: complexation / 4.2: Acetylation / 4.3: Oxidation / 5.1: Deacetylation / 6.1: Oxidation / 7.1: Condensation / 8.1: Alkylation / 9.1: deacetalization;

DOI:10.1021/jo0008688

Reference yield:

methyl (3β)-3-hydroxyurs-12-en-28-oate (915-32-2,26532-60-5,32208-45-0,74984-68-2,94482-47-0,121468-30-2) → methyl 23-benzyloxy-3-oxours-12-en-28-oate (303174-78-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Jones / acetone

2.1: NH₂OH*HCl; NaOAc / methanol; CH₂Cl₂

3.1: Na₂PdCl₄; NaOAc / acetic acid / 72 h

3.2: DMAP; Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

3.3: 1.92 g / Pb(OAc)4 / pyridine; tetrahydrofuran; acetic acid / 16 h / 20 °C

4.1: 98 percent / Na₂CO₃ / methanol / 16 h / 20 °C

5.1: 88 percent / 20percent HCl; NH₄OAc / TiCl₃ / H₂O; tetrahydrofuran / 4 h / 20 °C

6.1: 99 percent / PPTS; MS / benzene / 20 h / Heating

7.1: 94 percent / KH; n-Bu₄NI / tetrahydrofuran / 28 h / Heating

8.1: 91 percent / p-TsOH; PPTS / acetone / 48 h / 20 °C

With sodium tetrachloropalladate(II); hydroxylamine hydrochloride; ammonium acetate; sodium acetate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium carbonate; toluene-4-sulfonic acid; titanium(III) chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetone; benzene; 1.1: Oxidation / 2.1: oximation / 3.1: complexation / 3.2: Acetylation / 3.3: Oxidation / 4.1: Deacetylation / 5.1: Oxidation / 6.1: Condensation / 7.1: Alkylation / 8.1: deacetalization;

DOI:10.1021/jo0008688

upstream raw materials:

methyl 23-benzyloxy-3,3-ethylenedioxyurs-12-en-28-oate

ursolic acid

methyl (3β)-3-hydroxyurs-12-en-28-oate

methyl ursonate

Downstream raw materials:

methyl 23-benzyloxy-3α-hydroxyurs-12-en-28-oate

methyl 23-benzyloxy-3α-(tert-butyldimethyl)silyloxyurs-12-en-28-oate