[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

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Chemical Name:[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol
CAS No.:385809-29-0
Molecular Formula:C₂₆H₄₂O₅Si
Molecular Weight:462.702
Hs Code.:

Synonyms:[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

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Chemical Property of [1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

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Technology Process of [1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

There total 15 articles about [1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-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: 85.0%

: 385809-20-1
[1E,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-one

: 385809-29-0
[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

: 385809-21-2
[1E,3S,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -95 ℃; for 1.25h;
DOI:10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R

Reference yield:

: 387392-14-5
(1S)-1-{(4R,5R)-5-[(1S)-1-hydroxy-3-methyl-3-butenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methyl-3-buten-1-ol

: 385809-29-0
[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / KOtBu / 13 / 20 °C

2: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

3: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

4: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

5: 86 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 5 °C / 2.5 Torr

6: 10.6 percent / CeCl₃*7H₂O; naBh₄ / methanol / 1 h / -95 °C

With lead(IV) acetate; sodium tetrahydroborate; cerium(III) chloride; potassium tert-butylate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo026743f

Reference yield:

: 385809-17-6
(4S,5S)-4,5-bis-1-[(S)-allyloxy-3-methylbut-3-enyl]-2,2-dimethyl-[1,3]-dioxolane

: 385809-29-0
[1E,3R,4S]-4-(4-methoxybenzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-triethylsilanyloxy-hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

2: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

3: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

4: 86 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 5 °C / 2.5 Torr

5: 10.6 percent / CeCl₃*7H₂O; naBh₄ / methanol / 1 h / -95 °C

With lead(IV) acetate; sodium tetrahydroborate; cerium(III) chloride; sodium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo026743f