((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

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Chemical Name:((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane
CAS No.:882424-60-4
Molecular Formula:C₂₉H₄₆O₄Si
Molecular Weight:486.767
Hs Code.:

Synonyms:((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

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Chemical Property of ((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

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Technology Process of ((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

There total 5 articles about ((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane 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: 89.0%

: 882424-54-6
(R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-en-1-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 882424-60-4
((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/ol053092b

Reference yield:

: 1-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylprop-2-en-1-ol

: 882424-60-4
((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / 4-dimethylaminopyridine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂ / 0 - 45 °C

2: 100 percent / LiHMDS; TMSCl / tetrahydrofuran / 12 h / -78 - 20 °C

3: 79 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

4: 89 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; 2: Ireland-Claisen rearrangement;
DOI:10.1021/ol053092b

Reference yield:

: 882424-52-4
(S)-1-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylallyl 2-(4-methoxybenzyloxy)acetate

: 882424-60-4
((R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enyloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / LiHMDS; TMSCl / tetrahydrofuran / 12 h / -78 - 20 °C

2: 79 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

3: 89 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

With lithium aluminium tetrahydride; chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Ireland-Claisen rearrangement;
DOI:10.1021/ol053092b