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

Base Information

Chemical Name:(S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one
CAS No.:344357-19-3
Molecular Formula:C₂₀H₂₆O₇
Molecular Weight:378.422
Hs Code.:

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

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Chemical Property of (S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

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Technology Process of (S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

There total 11 articles about (S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one 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: 83.0%

: 125261-01-0
2-(2-phenyl-1,3-dioxolan-2-yl)acetaldehyde

: 202846-65-9
(3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

: 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

Guidance literature:: (3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2-(2-phenyl-1,3-dioxolan-2-yl)acetaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 3.5h;
DOI:10.1002/jhet.5570380124

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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