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

Base Information

• Chemical Name: (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate
• CAS No.: 637741-25-4
• Molecular Formula: C₅₇H₇₆O₁₂
• Molecular Weight: 953.223

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate 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-tetradeca-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 → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate (637741-25-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b305818b

Reference yield:

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (637742-08-6) → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate (637741-25-4)

Guidance literature:

Multi-step reaction with 17 steps

1: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 12 h / 0 °C

2: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3: 3.5 g / tetrahydrofuran / 12 h / Heating

4: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

5: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

6: tetrahydrofuran / Heating

7: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

8: tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 20 °C

9: 75 percent / tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

10: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

11: diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

12: tetrahydrofuran / Heating

13: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

14: 362 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

15: 89 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

16: dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 12 h / Heating

17: aq. HCl / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; 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 / 5: Swern oxidation / 6: Wittig reaction / 12: Wittig reaction;

DOI:10.1039/b305818b

Reference yield:

(2R,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexanal → (1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate (637741-25-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 3.5 g / tetrahydrofuran / 12 h / Heating

2: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

3: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: tetrahydrofuran / Heating

5: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

6: tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 20 °C

7: 75 percent / tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

8: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

9: diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

10: tetrahydrofuran / Heating

11: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

12: 362 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

13: 89 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

14: dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 12 h / Heating

15: aq. HCl / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; 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; 1: Wittig reaction / 3: Swern oxidation / 4: Wittig reaction / 10: Wittig reaction;

DOI:10.1039/b305818b

upstream raw materials:

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2S,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexan-1-ol

(E)-(4S,5R,6S)-5-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-oct-2-en-1-ol

ethyl (2E,4S,5R,6S)-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-2-octenoate

Downstream raw materials:

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

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