(S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one
• CAS No.: 344357-32-0
• Molecular Formula: C₂₄H₃₆O₇
• Molecular Weight: 436.546

Synonyms:(S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

Chemical Property of (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

There total 13 articles about (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-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: 84.0%

(3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone (202846-65-9) + (3R,4S)-3-(4-methoxybenzyloxy)-4-methylhexanal (344357-18-2) → (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one (344357-32-0)

Guidance literature:

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

(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhexanal; In tetrahydrofuran; hexane; at -78 ℃; for 3.5h;

DOI:10.1002/jhet.5570380124

Reference yield:

diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate (73840-71-8) → (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one (344357-32-0)

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 / -78 °C

8.2: 84 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:

(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester (202846-62-6) → (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one (344357-32-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / aq. KOH / methanol / 72 h / 20 °C

2.1: 74 percent / lithium triethylborohydride / tetrahydrofuran / 40 h / 20 °C

3.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / Heating

4.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 44 h / 20 °C

5.1: 88 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C

6.1: 76 percent / 30 percent aq. H₂O₂ / tetrahydrofuran / 5 h / 20 °C

7.1: LDA / tetrahydrofuran; hexane / -78 °C

7.2: 84 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

upstream raw materials:

(3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhexanal

(2S,3S)-3-Methyl-pentane-1,2-diol

(2S,3S)-1,2-Epoxy-3-methylpentane

Downstream raw materials:

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

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

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