(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

Base Information

Chemical Name:(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate
CAS No.:637740-92-2
Molecular Formula:C₇₇H₁₀₀O₁₂Si
Molecular Weight:1245.72
Hs Code.:

(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

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Chemical Property of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

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Technology Process of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

There total 8 articles about (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate 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,2S,3R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

: (2E,6E,8E)-(4R,5R,10S,11R,12S)-11-Acetoxy-5-hydroxy-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

: 637740-92-2
(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

Guidance literature:: With hydrogen fluoride; In acetonitrile; at -10 ℃; for 3h;
DOI:10.1039/b305818b

Reference yield:

: 361525-06-6
1-Methoxy-4-[(1R,2S)-2-methyl-1-((S)-1-methyl-but-2-ynyl)-dodecyloxymethyl]-benzene

: 637740-92-2
(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 9-borabicyclo[3.3.1]nonane dimer; hydrogen fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: Suzuki-Miyaura coupling;
DOI:10.1039/b305818b

Reference yield:

: 361525-03-3
(2E,6E)-(4R,5R)-7-Iodo-2,4,6-trimethyl-5-triphenylsilanyloxy-hepta-2,6-dienoic acid ethyl ester

: 637740-92-2
(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5R,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triphenylsiloxy)-11-acetoxy-2,6,8-docosatrienoate

Guidance literature:: Multi-step reaction with 6 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

With 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; 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