(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

Base Information

Chemical Name:(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol
CAS No.:233589-85-0
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

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Chemical Property of (E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

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Technology Process of (E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

There total 9 articles about (E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-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: 72.0%

: 233589-84-9
(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester

: 233589-85-0
(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

: 100-39-0
benzyl bromide

: 233589-85-0
(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / dimethylformamide

2: TBAF / tetrahydrofuran

3: imidazole; 2,4,5-triiodoimidazole; (Ph)2P / toluene / Heating

4: 99 percent / Zn / ethanol / Heating

5: methanol

6: 72 percent / LiAlH₄ / tetrahydrofuran / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,4,5-triiodoimidazole; tetrabutyl ammonium fluoride; sodium hydride; diphenylphosphane; zinc; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Hydrolysis / 3: Substitution / 4: Rearrangement / 5: Condensation / 6: Reduction;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

: 73111-80-5
(2R,3S,4S)-3,4-isopropylidenedioxy-2-benzyloxyhex-5-enal

: 233589-85-0
(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: methanol

2: 72 percent / LiAlH₄ / tetrahydrofuran / 0 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; methanol; 1: Condensation / 2: Reduction;
DOI:10.1016/S0040-4039(99)00911-9