(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

Base Information

• Chemical Name: (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
• CAS No.: 331625-65-1
• Molecular Formula: C₆₅H₉₂O₁₂
• Molecular Weight: 1065.44

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (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

There total 33 articles about (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 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:

(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 (331625-64-0) → (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 (331625-65-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ja0057272

Reference yield:

D-arabinofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (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 (331625-65-1)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂SO₄ / dimethylformamide / 90 °C

2: Bu₄NBr; KOH / tetrahydrofuran; H₂O / 90 °C

3: 95 percent / DIBAL; NiCl₂(dppp) / diethyl ether / 20 °C

4: LiAlH₄ / tetrahydrofuran / 20 °C

5: 93 percent / triethylamine / CH₂Cl₂ / 20 h / 20 °C

6: DCC; DMAP; DMAP*HCl / CH₂Cl₂ / 12 h / Heating

7: 336 mg / aq. HCl / tetrahydrofuran / 12 h / 20 °C

With hydrogenchloride; dmap; potassium hydroxide; lithium aluminium tetrahydride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutylammomium bromide; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; sulfuric acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 6: Keck's reaction;

DOI:10.1021/ja0057272

Reference yield:

caprinaldehyde (112-31-2) → (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 (331625-65-1)

Guidance literature:

Multi-step reaction with 25 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

21: 96 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

22: 90 percent / tetrapropylammonium perruthenate; NMO / CH₂Cl₂ / 1 h / 20 °C

23: 83 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

24: DCC; DMAP; DMAP*HCl / CH₂Cl₂ / 12 h / Heating

25: 336 mg / aq. HCl / tetrahydrofuran / 12 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; lithium borohydride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-(dimethylamino)pyridine hydrochloride; tin(II) oxide; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 5: Swern oxidation / 10: Swern oxidation / 11: Wittig olefination / 14: Wittig olefination / 20: Wittig olefination / 24: Keck's reaction;

DOI:10.1021/ja0057272

upstream 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

caprinaldehyde

D-arabinofuranose

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(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

khafrefungin

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

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