(5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester

Base Information

• Chemical Name: (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester
• CAS No.: 131138-03-9
• Molecular Formula: C₂₈H₃₈O₃Si
• Molecular Weight: 450.693

Synonyms:(5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester

Chemical Property of (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester

Chemical Property:

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Technology Process of (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester

There total 7 articles about (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl 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: 85.0%

11-(tert-butyldiphenylsilanyloxy)undeca-5,8-diynoic acid methyl ester → (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester (131138-03-9)

Guidance literature:

With sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine; In methanol; at 20 ℃; for 2h;

DOI:10.1002/chem.200902880

Reference yield:

4-(tert-butyldiphenylsilyloxy)-1-butyne (88158-68-3) → (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester (131138-03-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) LiNH₂/NH₃ / 1) hexane, 2) 5h

2: 97 percent / H₂ / Ni(OAc)2*4H₂O, NaBH₄ / ethanol / 0.25 h / 760 Torr

3: 1) MsCl, NEt₃, 2) NaI / 1) CH₂Cl₂, RT, 0.5h, 2) acetone, 2h, reflux

4: 100 percent / acetonitrile / 48 h / Heating

5: 1) BuLi, HMPA / 1) THF, hexane, -78 deg C, 45 min, 2) THF, -78 deg C to RT

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium amide; ammonia; hydrogen; methanesulfonyl chloride; triethylamine; sodium iodide; sodium tetrahydroborate; nickel diacetate; In ethanol; acetonitrile;

DOI:10.1016/S0040-4020(01)96002-8

Reference yield:

6-((tert-butyldiphenylsilyl)oxy)hex-3-yn-1-ol (122069-55-0) → (5Z,8Z)-11-[(tert-butyldiphenylsilyl)oxy]undeca-5,8-dienoic acid methyl ester (131138-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / Ni(OAc)2*4H₂O, NaBH₄ / ethanol / 0.25 h / 760 Torr

2: 1) MsCl, NEt₃, 2) NaI / 1) CH₂Cl₂, RT, 0.5h, 2) acetone, 2h, reflux

3: 100 percent / acetonitrile / 48 h / Heating

4: 1) BuLi, HMPA / 1) THF, hexane, -78 deg C, 45 min, 2) THF, -78 deg C to RT

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen; methanesulfonyl chloride; triethylamine; sodium iodide; sodium tetrahydroborate; nickel diacetate; In ethanol; acetonitrile;

DOI:10.1016/S0040-4020(01)96002-8

upstream raw materials:

methyl 4-formylbutanoate

[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-hex-3-enyl]-triphenyl-phosphonium; iodide

methyl 4-(chlorocarbonyl)butyrate

4-(tert-butyldiphenylsilyloxy)-1-butyne

Downstream raw materials:

((Z,Z) methyl 5,8-undecadienoate-11-yl)triphenylphosphonium iodide

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