[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane
CAS No.:404339-10-2
Molecular Formula:C₂₈H₄₈O₄Si
Molecular Weight:476.772
Hs Code.:

Synonyms:[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

There total 18 articles about [(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane 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: 92.0%

: 404338-80-3
{(1S)-6-[(1R,2R,4S)-2-(benzyloxymethyl)-4-(methoxymethoxy)cyclopentyl]-1-methylhex-5-ynyloxy}-tert-butyldimethylsilane

: 404339-10-2
[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In hexane; at 20 ℃; for 8h;
DOI:10.1021/jo010744a

Reference yield:

: 100-39-0
benzyl bromide

: 404339-10-2
[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 20 °C

2: pyridinium tribromide; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 82 percent / NaNH₂ / tetrahydrofuran; liquid ammonia / 0.5 h / Heating

4: 81 percent / nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0 - 20 °C

5: 92 percent / H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 20 °C

With pyridine; quinoline; n-butyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium amide; pyridinium hydrobromide perbromide; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; ammonia; N,N-dimethyl-formamide;
DOI:10.1021/jo010744a

Reference yield:

: 89408-85-5
(S)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

: 404339-10-2
[(Z)-(S)-6-((1S,2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-cyclopentyl)-1-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 13 steps

1.1: 97 percent / DMAP; Et₃N / CH₂Cl₂ / 72 h / 20 °C

2.1: CuI / tetrahydrofuran / 0.5 h / -35 °C

2.2: 83 percent / tetrahydrofuran / 1 h / -35 - -25 °C

3.1: 88 percent / Ti(O-i-Pr)4 / 24 h / Heating

4.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

5.1: 96 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 96 percent / Ph₃P; imidazole; I₂ / tetrahydrofuran / 3 h / 20 °C

7.1: 92 percent / LHMDS / tetrahydrofuran / 0.5 h / 0 °C

8.1: 100 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

9.1: 96 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 20 °C

10.1: pyridinium tribromide; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 82 percent / NaNH₂ / tetrahydrofuran; liquid ammonia / 0.5 h / Heating

12.1: 81 percent / nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0 - 20 °C

13.1: 92 percent / H₂; quinoline / Pd/CaCO₃/Pb / hexane / 8 h / 20 °C

With pyridine; 1H-imidazole; quinoline; titanium(IV) isopropylate; dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium amide; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; ammonia; N,N-dimethyl-formamide;
DOI:10.1021/jo010744a