(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

Base Information

• Chemical Name: (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
• CAS No.: 637740-94-4
• Molecular Formula: C₇₅H₉₄O₁₁Si
• Molecular Weight: 1199.65

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 12 articles about (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 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: 40.0%

(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 (637740-93-3) → (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 (637740-94-4)

Guidance literature:

(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; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

With dmap; In tetrahydrofuran; toluene; for 15h; Further stages.; Heating;

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) → (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 (637740-94-4)

Guidance literature:

Multi-step reaction with 8 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

7.1: 48 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.17 h / -78 °C

8.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

8.2: 40 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 15 h / Heating

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3.1: Suzuki-Miyaura coupling;

DOI:10.1039/b305818b

Reference yield:

(2E,4R,5R,6E)-2,4,6-trimethyl-5-(triphenylsiloxy)-7-iodo-2,6-heptadien-1-ol (361525-04-4) → (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 (637740-94-4)

Guidance literature:

Multi-step reaction with 9 steps

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

2.1: 1.27 g / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

3.1: 79 percent / N,N-dimethylaminopyridine; dicyclohexylcarbodiimide; N,N-dimethylaminopyridine hydrogenchloride / CH₂Cl₂ / 6 h / Heating

4.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

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

5.1: 692 mg / aq. hydrogen fluoride / acetonitrile / 3 h / -10 °C

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

7.1: 462 mg / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

8.1: 48 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.17 h / -78 °C

9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

9.2: 40 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 15 h / Heating

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; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3.1: Keck's esterification / 4.1: Suzuki-Miyaura coupling;

DOI:10.1039/b305818b

upstream raw materials:

(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

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

Downstream raw materials:

(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

(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

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