(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate

Base Information

• Chemical Name: (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate
• CAS No.: 637741-19-6
• Molecular Formula: C₇₅H₁₁₆O₁₂Si₂
• Molecular Weight: 1265.91

Synonyms:(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate

Chemical Property of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate

There total 19 articles about (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-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: 65.0%

(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol (331626-81-4) + (2E,6E,8E)-(4R,5S,11R)-11-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid (637742-06-4) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate (637741-19-6)

Guidance literature:

With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; In dichloromethane; for 48h; Heating;

DOI:10.1039/b305818b

Reference yield:

2-(4-methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane (288402-96-0) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate (637741-19-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 20 h / 0 °C

2: 84 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

3: tetrahydrofuran / 12 h / Heating

4: 2.67 g / diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

5: 89 percent / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

6: tetrahydrofuran / Heating

7: 1.98 g / diisobutylaluminun hydride / CH₂Cl₂; hexane / -78 °C

8: 95 percent / manganese(IV) oxide / CH₂Cl₂ / 15 h / 20 °C

9: 78 percent / tin(II) trifluoromethanesufonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

10: 85 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

11: 95 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.08 h / -78 °C

12: 98 percent / CH₂Cl₂ / Heating

13: 87 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

14: manganese(IV) oxide / CH₂Cl₂ / 20 °C

15: 91 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

16: 65 percent / dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 48 h / Heating

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; 2-methyl-but-2-ene; oxalyl dichloride; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 2: Swern oxidation / 3: Wittig reaction / 6: Wittig reaction / 12: Wittig reaction;

DOI:10.1039/b305818b

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-(tert-butyldimethylsiloxy)butyl (2E,4R,5S,6E,8E,11R)-2,4,6,8-tetramethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatrienoate (637741-19-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

2: 95 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.08 h / -78 °C

3: 98 percent / CH₂Cl₂ / Heating

4: 87 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

5: manganese(IV) oxide / CH₂Cl₂ / 20 °C

6: 91 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 15 h / 20 °C

7: 65 percent / dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 48 h / Heating

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In hexane; dichloromethane; water; tert-butyl alcohol; 3: Wittig reaction;

DOI:10.1039/b305818b

upstream raw materials:

(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol

(2E,6E,8E)-(4R,5S,11R)-11-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-5-triethylsilanyloxy-docosa-2,6,8-trienoic acid

2-(4-methoxyphenyl)-4-(R)-undecyl-[1,3]dioxane

triethylsilyl trifluoromethyl sulfonate

Downstream raw materials:

(2E,6E,8E)-(4R,11R)-11-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-5-oxo-docosa-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

(2E,6E,8E)-(4R,5S,11R)-5-Hydroxy-11-(4-methoxy-benzyloxy)-2,4,6,8-tetramethyl-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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