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

Base Information

• Chemical Name: (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid ethyl ester
• CAS No.: 331625-61-7
• Molecular Formula: C₄₄H₇₆O₅Si
• Molecular Weight: 713.17

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 22 articles about (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-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:

caprinaldehyde (112-31-2) → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid ethyl ester (331625-61-7)

Guidance literature:

Multi-step reaction with 20 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: LiBH₄ / tetrahydrofuran / -5 °C

8: 95 percent / TsOH / CH₂Cl₂ / 20 °C

9: 96 percent / DIBAL / CH₂Cl₂; hexane / 20 °C

10: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

11: tetrahydrofuran / Heating

12: 98 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

13: 88 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

14: 87 percent / tetrahydrofuran / Heating

15: 97 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

16: 93 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

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

18: 84 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

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

20: tetrahydrofuran / Heating

With pyridine; 2,6-dimethylpyridine; 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; 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid ethyl ester (331625-61-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / TsOH / CH₂Cl₂ / 20 °C

2: 96 percent / DIBAL / CH₂Cl₂; hexane / 20 °C

3: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: tetrahydrofuran / Heating

5: 98 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

6: 88 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

7: 87 percent / tetrahydrofuran / Heating

8: 97 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

9: 93 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

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

11: 84 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

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

13: tetrahydrofuran / Heating

With 2,6-dimethylpyridine; 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; hexane; dichloromethane; 3: Swern oxidation / 4: Wittig olefination / 7: Wittig olefination / 13: Wittig olefination;

DOI:10.1021/ja0057272

Reference yield:

(2S)-2-methyl-1-dodecanol (57289-26-6) → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid ethyl ester (331625-61-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 91 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

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

3: LiBH₄ / tetrahydrofuran / -5 °C

4: 95 percent / TsOH / CH₂Cl₂ / 20 °C

5: 96 percent / DIBAL / CH₂Cl₂; hexane / 20 °C

6: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7: tetrahydrofuran / Heating

8: 98 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

9: 88 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

10: 87 percent / tetrahydrofuran / Heating

11: 97 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

12: 93 percent / TPAP; NMO / CH₂Cl₂ / 20 °C

13: 90 percent / Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / -78 °C

14: 84 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

15: 96 percent / DIBAL / CH₂Cl₂; hexane / -78 °C

16: tetrahydrofuran / Heating

With 2,6-dimethylpyridine; lithium borohydride; 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; hexane; dichloromethane; 1: Swern oxidation / 6: Swern oxidation / 7: Wittig olefination / 10: Wittig olefination / 16: Wittig olefination;

DOI:10.1021/ja0057272

upstream raw materials:

(carbethoxyethylidene)triphenylphosphorane

(4E,6E)-(2S,3S,8S,9R,10S)-9-(4-Methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-3-triethylsilanyloxy-icosa-4,6-dienal

caprinaldehyde

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2S,3R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

(2E,6E,8E)-(4R,5S,10S,11R,12S)-5-Hydroxy-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-docosa-2,6,8-trienoic acid (1R,2S,3R)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

(2E,6E,8E)-(4R,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid (1R,2R,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butyl ester

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