7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl ester

Base Information

• Chemical Name: 7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl ester
• CAS No.: 57289-51-7
• Molecular Weight: 376.49
• Mol file: 57289-51-7.mol

Synonyms:7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl ester

Chemical Property of 7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl ester

There total 14 articles about 7-Oxocass-13(15)-ene-16,19-dioic acid dimethyl 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:

13-Oxopodocarp-8(14)-en-18-saeure-methylester (20085-81-8) → (1R,4aR,4bS,8R,8aR,10aR)-7-[1-Methoxycarbonyl-meth-(E)-ylidene]-1,4a,8-trimethyl-9-oxo-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester (57289-51-7,109278-74-2,109278-76-4,128573-32-0,128573-33-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / Ac₂O,H(+)

2: m-chloroperbenzoic acid / ethanol / 2 h / 0 °C

3: H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

4: PPTS / CH₂Cl₂ / 2 h / Ambient temperature

5: tetrahydrofuran / -78 °C

7: tetrahydrofuran / 0.25 h / -30 °C

8: 75 percent / hexamethylphosphoric acid triamide / 0.5 h / -30 °C

9: H₂ / 5percent Pd/C / ethyl acetate

10: tetrahydrofuran / 4 h / -78 °C

11: PPTS / ethanol / 24 h / 55 °C

12: pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; hydrogen cation; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)84778-4

Reference yield:

Methyl 7α-hydroxy-13-oxopodocarp-8(14)-en-18-oate (25594-20-1) → (1R,4aR,4bS,8R,8aR,10aR)-7-[1-Methoxycarbonyl-meth-(E)-ylidene]-1,4a,8-trimethyl-9-oxo-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester (57289-51-7,109278-74-2,109278-76-4,128573-32-0,128573-33-1)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

2: PPTS / CH₂Cl₂ / 2 h / Ambient temperature

3: tetrahydrofuran / -78 °C

5: tetrahydrofuran / 0.25 h / -30 °C

6: 75 percent / hexamethylphosphoric acid triamide / 0.5 h / -30 °C

7: H₂ / 5percent Pd/C / ethyl acetate

8: tetrahydrofuran / 4 h / -78 °C

9: PPTS / ethanol / 24 h / 55 °C

10: pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogen; pyridinium p-toluenesulfonate; pyridinium chlorochromate; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)84778-4

Reference yield:

Methyl 7α-hydroxy-13-oxo-(8αH)-podocarpan-18-oate (109164-57-0) → (1R,4aR,4bS,8R,8aR,10aR)-7-[1-Methoxycarbonyl-meth-(E)-ylidene]-1,4a,8-trimethyl-9-oxo-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester (57289-51-7,109278-74-2,109278-76-4,128573-32-0,128573-33-1)

Guidance literature:

Multi-step reaction with 9 steps

1: PPTS / CH₂Cl₂ / 2 h / Ambient temperature

2: tetrahydrofuran / -78 °C

4: tetrahydrofuran / 0.25 h / -30 °C

5: 75 percent / hexamethylphosphoric acid triamide / 0.5 h / -30 °C

6: H₂ / 5percent Pd/C / ethyl acetate

7: tetrahydrofuran / 4 h / -78 °C

8: PPTS / ethanol / 24 h / 55 °C

9: pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogen; pyridinium p-toluenesulfonate; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)84778-4

upstream raw materials:

diazomethane

cassamic acid

cassamine

(1R,4aR,4bS,8R,8aR,9R,10aR)-9-Hydroxy-7-[1-methoxycarbonyl-meth-(E)-ylidene]-1,4a,8-trimethyl-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester

Refernces