(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
CAS No.:218439-09-9
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Chemical Property of (4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Technology Process of (4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 8 articles about (4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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: 99.0%

: 218439-36-2
[(4R,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

: 218439-09-9
(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; for 0.0833333h; Ambient temperature;
DOI:10.1246/bcsj.71.2433

Reference yield:

: 105368-84-1
4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose

: 218439-09-9
(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 1 h / 0 - 5 °C

2: 68 percent / Hg(OAc)2 / Heating

3: 97 percent / decahydronaphthalene / 0.25 h / 200 °C

4: 99 percent / NaBH₄ / ethanol / 0.17 h / 0 °C

5: 228 mg / i-Pr₂NEt, NaI / tetrahydrofuran / 48 h / Ambient temperature

6: 114 mg / n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

7: 99 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 0.08 h / Ambient temperature

With pyridine; sodium tetrahydroborate; mercury(II) diacetate; tetrabutyl ammonium fluoride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; decalin;
DOI:10.1246/bcsj.71.2433

Reference yield:

: 218439-03-3
tert-Butyl-[(4R,5S)-2,2-dimethyl-5-(1-vinyloxy-allyl)-[1,3]dioxolan-4-ylmethoxy]-diphenyl-silane

: 218439-09-9
(4S,5S)-5-((E)-5-Benzyloxymethoxy-pent-1-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / decahydronaphthalene / 0.25 h / 200 °C

2: 99 percent / NaBH₄ / ethanol / 0.17 h / 0 °C

3: 228 mg / i-Pr₂NEt, NaI / tetrahydrofuran / 48 h / Ambient temperature

4: 114 mg / n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

5: 99 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 0.08 h / Ambient temperature

With pyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; decalin;
DOI:10.1246/bcsj.71.2433