(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Base Information

Chemical Name:(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol
CAS No.:600737-51-7
Molecular Formula:C₄₇H₉₀O₇Si₂
Molecular Weight:823.398
Hs Code.:

Synonyms:(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

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Chemical Property of (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

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Technology Process of (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

There total 12 articles about (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol 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:

: 132969-60-9
(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

: 600737-51-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

1.2: 20.09 g / CH₂Cl₂ / 12 h / -78 - 20 °C

2.1: 86 percent / trimethylaluminium / tetrahydrofuran; benzene / 3.5 h / 0 °C

3.1: 13.0 g / diisopropylethylamine; (ⁿBu)4N⁽¹⁺⁾*I^(1-) / 2.5 h / 0 °C

4.1: 10.8 g / tetrahydrofuran; diethyl ether / 7 h / 0 °C

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1.2: Evans aldol reaction;
DOI:10.1021/jo034521r

Reference yield:

: 136320-64-4
(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol

: 600737-51-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / -78 °C

2.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.2: 20.09 g / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 86 percent / trimethylaluminium / tetrahydrofuran; benzene / 3.5 h / 0 °C

4.1: 13.0 g / diisopropylethylamine; (ⁿBu)4N⁽¹⁺⁾*I^(1-) / 2.5 h / 0 °C

5.1: 10.8 g / tetrahydrofuran; diethyl ether / 7 h / 0 °C

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1.1: Swern oxidation / 2.2: Evans aldol reaction;
DOI:10.1021/jo034521r

Reference yield:

: 184297-49-2
(2S,3R)-2-((S)-2-Benzyloxy-1-methyl-ethyl)-3,5-dimethyl-2,3-dihydro-pyran-4-one

: 600737-51-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-13-(4-Methoxy-benzyloxy)-11-methoxymethoxy-2,4,6,8,10,12-hexamethyl-3,9-bis-triisopropylsilanyloxy-tridec-5-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h / 0 °C

2: TsOH / tetrahydrofuran; H₂O / 7 h / Heating

3: 1.58 g / lithium borohydride / tetrahydrofuran / 4 h / 0 °C

4: 88 percent / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

5: triethylamine / CH₂Cl₂ / 24 h

6: 3.61 g / DIBAL-H / CH₂Cl₂; toluene / 0.33 h / -78 °C

7: 96 percent / triphenyl phosphite methiodide / dimethylformamide / 0.5 h

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; triphenyl phosphite methiodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Luche reduction / 2: Ferrier rearrangement;
DOI:10.1021/jo034521r