methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

Base Information

Chemical Name:methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate
CAS No.:122598-97-4
Molecular Formula:C₃₀H₄₀O₁₀
Molecular Weight:560.642
Hs Code.:

Synonyms:methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

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Chemical Property of methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

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Technology Process of methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

There total 13 articles about methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate 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%

: 122598-96-3
methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

: 122598-97-4
methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃;
DOI:10.1016/S0040-4039(00)82308-4

Reference yield:

: 122598-89-4
(3Z)-2-benzyloxy-6-<(2-tetrahydropyranyl)oxy>-4-methylhex-3-en-1-ol

: 122598-97-4
methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

Guidance literature:: Multi-step reaction with 7 steps

1: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) sodium hydride, 2.) potassium iodide / 1.) THF, DMF, room temperature, 0.5 h, 2.) reflux, 48 h

3: 88 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / Heating

4: 100 percent / triethylamine / CH₂Cl₂ / 0 °C

5: 1.) sodium hydride / 1.) THF, DMF, room temperature, 0.5 h, 2.) room temperature, 10 h

6: 1.) sodium hydride, 2.) potassium iodide / 1.) THF, DMF, room temperature, 0.5 h, 2.) 85 deg C, 6 h

7: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.75 h / Ambient temperature

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; potassium iodide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1139/v92-297

Reference yield:

: 145762-63-6
methyl (5Z)-4-benzyloxy-8-hydroxy-2-methoxycarbonyl-6-methyloct-5-enoate

: 122598-97-4
methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0 °C

2: 1.) sodium hydride / 1.) THF, DMF, room temperature, 0.5 h, 2.) room temperature, 10 h

3: 1.) sodium hydride, 2.) potassium iodide / 1.) THF, DMF, room temperature, 0.5 h, 2.) 85 deg C, 6 h

4: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.75 h / Ambient temperature

With tetrabutyl ammonium fluoride; sodium hydride; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1139/v92-297