(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

Base Information

Chemical Name:(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone
CAS No.:344357-20-6
Molecular Formula:C₂₀H₂₄O₇
Molecular Weight:376.406
Hs Code.:

Synonyms:(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

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Chemical Property of (3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

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Technology Process of (3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

There total 13 articles about (3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 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: 54.0%

: 344357-19-3
(S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

: 344357-25-1
(3R,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

: 344357-20-6
(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 1.5h;
DOI:10.1002/jhet.5570380124

Reference yield:

: 73840-71-8
diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate

: 344357-20-6
(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

Guidance literature:: Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: 67 percent / tetrahydrofuran; hexane / 21 h / -78 - 0 °C

2.1: 97 percent / aq. KOH / methanol / 72 h / 20 °C

3.1: 74 percent / lithium triethylborohydride / tetrahydrofuran / 40 h / 20 °C

4.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / Heating

5.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 44 h / 20 °C

6.1: 88 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C

7.1: 76 percent / 30 percent aq. H₂O₂ / tetrahydrofuran / 5 h / 20 °C

8.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 83 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

9.1: 38 percent / Jones reagent / acetone / 1.5 h / 0 °C

With potassium hydroxide; jones reagent; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetone;
DOI:10.1002/jhet.5570380124

Reference yield:

: 202846-63-7
(3S,4S)-4-(2-benzyloxyethyl)-3-hydroxy-4-methyl-γ-butyrolactone

: 344357-20-6
(3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / Heating

2.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 44 h / 20 °C

3.1: 88 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C

4.1: 76 percent / 30 percent aq. H₂O₂ / tetrahydrofuran / 5 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 83 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

6.1: 38 percent / Jones reagent / acetone / 1.5 h / 0 °C

With jones reagent; tributylphosphine; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;
DOI:10.1002/jhet.5570380124