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

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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-en-1-ol
CAS No.:882424-54-6
Molecular Formula:C₂₃H₃₂O₄
Molecular Weight:372.505
Hs Code.:

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

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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-en-1-ol

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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-en-1-ol

There total 4 articles about (R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-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: 79.0%

: 882424-53-5
(R,E)-5-((2S,6S)-6-allyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-(4-methoxybenzyloxy)-4-methylpent-4-enoic acid

: 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

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h;
DOI:10.1021/ol053092b

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

With dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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