(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

Base Information

Chemical Name:(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
CAS No.:637742-11-1
Molecular Formula:C₃₃H₅₆O₄SSi
Molecular Weight:576.957
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 637741-23-2
S-ethyl (2S,3S,4E,6E,8S,9R,10S)-2,4,6,8,10-pentamethyl-3-hydroxy-9-(4-methoxybenzyloxy)-4,6-dodecadienethioate

: 637742-11-1
(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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1039/b305818b

Reference yield:

: 637742-08-6
(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

: 637742-11-1
(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

Guidance literature:: Multi-step reaction with 10 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

With 2,6-dimethylpyridine; 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

: 637742-11-1
(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

Guidance literature:: Multi-step reaction with 8 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

With 2,6-dimethylpyridine; 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