S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate

Base Information

• Chemical Name: S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate
• CAS No.: 637741-23-2
• Molecular Formula: C₂₇H₄₂O₄S
• Molecular Weight: 462.694

Synonyms:S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate

Chemical Property of S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate

There total 9 articles about S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate 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: 75.0%

(Z)-1-ethylthio-1-(trimethylsiloxy)propene (63584-42-9,130535-66-9,63584-50-9) + (2E,4E)-(6S,7R,8S)-7-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-deca-2,4-dienal → S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate (637741-23-2)

Guidance literature:

With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; In dichloromethane; at -78 ℃; for 16h;

DOI:10.1039/b305818b

Reference yield:

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (637742-08-6) → S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate (637741-23-2)

Guidance literature:

Multi-step reaction with 9 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

With tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2: Swern oxidation / 3: Wittig reaction / 5: Swern oxidation / 6: Wittig reaction;

DOI:10.1039/b305818b

Reference yield:

(2R,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexanal → S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate (637741-23-2)

Guidance literature:

Multi-step reaction with 7 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

With tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Wittig reaction / 3: Swern oxidation / 4: Wittig reaction;

DOI:10.1039/b305818b

upstream raw materials:

(Z)-1-ethylthio-1-(trimethylsiloxy)propene

(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

Downstream raw materials:

(4E,6E)-(2S,3S,8S,9R,10S)-9-(4-Methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-3-triethylsilanyloxy-dodeca-4,6-dienethioic acid S-ethyl ester

(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

(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

(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 ethyl ester

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