(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

Base Information

Chemical Name:(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester
CAS No.:331626-27-8
Molecular Formula:C₃₈H₆₀O₅
Molecular Weight:596.891
Hs Code.:

Synonyms:(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

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Chemical Property of (2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

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Technology Process of (2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

There total 23 articles about (2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl 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: 77.0%

: 331625-53-7
(2E,6E,8E)-(4R,5S,10R,11R,12S)-5-Hydroxy-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-docosa-2,6,8-trienoic acid ethyl ester

: 331626-27-8
(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 0 ℃; for 15h;
DOI:10.1021/ja0057272

Reference yield:

: 112-31-2
caprinaldehyde

: 331626-27-8
(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 22 steps

1: 83 percent / Sn(OTf)2; SnO; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / 5 h / -78 °C

2: pyridine / 1,2-dichloro-ethane / 0.17 h / Heating

3: Bu₃SnH; AIBN / toluene / 0.17 h / 110 °C

4: 5.17 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 91 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

6: Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / -78 °C

7: 93 percent / LiBH₄ / tetrahydrofuran / 12 h / -5 °C

8: 88 percent / TsOH / CH₂Cl₂ / 12 h / 20 °C

9: 98 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

10: 92 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

11: tetrahydrofuran / 12 h / Heating

12: 96 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

13: 90 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 1 h / 20 °C

14: tetrahydrofuran / 12 h / Heating

15: 87 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

16: 93 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 1 h / 20 °C

17: 90 percent / Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / 16 h / -78 °C

18: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

19: 96 percent / DIBAL / CH₂Cl₂; hexane / 0.08 h / -78 °C

20: tetrahydrofuran / 12 h / Heating

21: 94 percent / aq. HCl / ethanol / 12 h / 20 °C

22: 77 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 15 h / 0 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium aluminium tetrahydride; lithium borohydride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tin(II) oxide; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; toluene; 5: Swern oxidation / 10: Swern oxidation / 11: Wittig olefination / 14: Wittig olefination / 20: Wittig olefination;
DOI:10.1021/ja0057272

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 331626-27-8
(2E,6E,8E)-(4R,10R,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 88 percent / TsOH / CH₂Cl₂ / 12 h / 20 °C

2: 98 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

3: 92 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: tetrahydrofuran / 12 h / Heating

5: 96 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

6: 90 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 1 h / 20 °C

7: tetrahydrofuran / 12 h / Heating

8: 87 percent / DIBAL / CH₂Cl₂; hexane / 0.25 h / -78 °C

9: 93 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 1 h / 20 °C

10: 90 percent / Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / 16 h / -78 °C

11: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

12: 96 percent / DIBAL / CH₂Cl₂; hexane / 0.08 h / -78 °C

13: tetrahydrofuran / 12 h / Heating

14: 94 percent / aq. HCl / ethanol / 12 h / 20 °C

15: 77 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 15 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; 3: Swern oxidation / 4: Wittig olefination / 7: Wittig olefination / 13: Wittig olefination;
DOI:10.1021/ja0057272