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

Base Information

Chemical Name:methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate
CAS No.:122598-96-3
Molecular Formula:C₄₆H₅₈O₁₀Si
Molecular Weight:799.046
Hs Code.:

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

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Chemical Property of methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

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Technology Process of methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

There total 12 articles about methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-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:

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

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 122598-86-1
2-benzyloxy-3-<(tert-butyldiphenylsilyl)oxy>-propanal

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

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) butyllithium / 1.) THF, hexane, -78 deg C to 0 deg C, ca. 0.5 h, 2.) THF, 0 deg C, 10 min

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

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

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

5: 88 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / Heating

6: 100 percent / triethylamine / CH₂Cl₂ / 0 °C

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

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

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