(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

Base Information

Chemical Name:(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene
CAS No.:676236-00-3
Molecular Formula:C₂₆H₄₂O₃Si
Molecular Weight:430.703
Hs Code.:

Synonyms:(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

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Chemical Property of (1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

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Technology Process of (1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

There total 7 articles about (1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene 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: 84.0%

: 676235-98-6
[(1S,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopenten-1-yl]ethanal

: [5-(4-methoxy-benzyloxy)-pentyl]-triphenyl-phosphonium; bromide

: 676236-00-3
(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

Guidance literature:: [5-(4-methoxy-benzyloxy)-pentyl]-triphenyl-phosphonium; bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.5h;

[(1S,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopenten-1-yl]ethanal; In tetrahydrofuran; at -70 - 20 ℃;
DOI:10.1016/j.tet.2006.01.051

Reference yield:

: 115074-49-2
(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate

: 676236-00-3
(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

1.2: 93 percent / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 50 °C

2.1: 89 percent / KI / H₂O; various solvent(s) / 10 h / 130 °C

3.1: 89 percent / (i-Bu)2AlH / CH₂Cl₂; hexane / 0.75 h / -78 °C

4.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C

4.2: 84 percent / tetrahydrofuran / -70 - 20 °C

With potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium iodide; In tetrahydrofuran; hexane; dichloromethane; water; 4.2: Wittig reaction;
DOI:10.1016/j.tet.2006.01.051

Reference yield:

: 426226-00-8
dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate

: 676236-00-3
(1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / KI / H₂O; various solvent(s) / 10 h / 130 °C

2.1: 89 percent / (i-Bu)2AlH / CH₂Cl₂; hexane / 0.75 h / -78 °C

3.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C

3.2: 84 percent / tetrahydrofuran / -70 - 20 °C

With sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium iodide; In tetrahydrofuran; hexane; dichloromethane; water; 3.2: Wittig reaction;
DOI:10.1016/j.tet.2006.01.051