(2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

Base Information

• Chemical Name: (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester
• CAS No.: 637741-48-1
• Molecular Formula: C₇₇H₉₈O₁₃Si
• Molecular Weight: 1259.7

Synonyms:(2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

Chemical Property of (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

There total 9 articles about (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl 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,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butyl ester → (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester (637741-48-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 20h;

DOI:10.1039/b305818b

Reference yield:

1-Methoxy-4-[(1R,2S)-2-methyl-1-((S)-1-methyl-but-2-ynyl)-dodecyloxymethyl]-benzene (361525-06-6) → (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester (637741-48-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

2.1: pyridine / CH₂Cl₂ / 3 h / 20 °C

2.2: 938 mg / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

3.2: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide; H₂O / 0.5 h / 65 °C

4.1: 692 mg / aq. hydrogen fluoride / acetonitrile / 3 h / -10 °C

5.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

6.1: 462 mg / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; hydrogen fluoride; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3.1: Suzuki-Miyaura coupling;

DOI:10.1039/b305818b

Reference yield:

(2E,6E)-(4R,5R)-7-Iodo-2,4,6-trimethyl-5-triphenylsilanyloxy-hepta-2,6-dienoic acid ethyl ester (361525-03-3) → (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-2,4,6,8,10,12-hexamethyl-5-triphenylsilanyloxy-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester (637741-48-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

2.1: manganese dioxide / CH₂Cl₂ / 12 h / 20 °C

3.1: 1.27 g / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

4.1: 79 percent / N,N-dimethylaminopyridine; dicyclohexylcarbodiimide; N,N-dimethylaminopyridine hydrogenchloride / CH₂Cl₂ / 6 h / Heating

5.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

5.2: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide; H₂O / 0.5 h / 65 °C

6.1: 692 mg / aq. hydrogen fluoride / acetonitrile / 3 h / -10 °C

7.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

8.1: 462 mg / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

With pyridine; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; N,N-dimethylaminopyridine hydrogenchloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 4.1: Keck's esterification / 5.1: Suzuki-Miyaura coupling;

DOI:10.1039/b305818b

upstream raw materials:

1-Methoxy-4-[(1R,2S)-2-methyl-1-((S)-1-methyl-but-2-ynyl)-dodecyloxymethyl]-benzene

(2E,4R,5R,6E)-2,4,6-trimethyl-5-(triphenylsiloxy)-7-iodo-2,6-heptadien-1-ol

(2E,6E)-(4R,5R)-7-Iodo-2,4,6-trimethyl-5-triphenylsilanyloxy-hepta-2,6-dienoic acid ethyl ester

(4S,5R,6S)-4,6-dimethyl-5-acetoxy-2-hexadecyne

Downstream raw materials:

(8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione

(8E,12E,14E)-(3S,4R,5R,10R,11R,16S,17R)-11-Hydroxy-3,4-bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7-dione

(3S,4S,5R,8E,10R,11R,12E,14E,16S,17R)-3,4-bis(4-methoxybenzyloxy)-5-[(4-methoxybenzyloxy)methyl]-8,10,12,14,16-pentamethyl-11-(triphenylsiloxy)-17-[(1S)-1-methylundecyl]-1,6-dioxa-8,12,14-cycloheptadecatriene-2,7-dione

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

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