(S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one
• CAS No.: 195321-27-8
• Molecular Formula: C₂₃H₂₃NO₆
• Molecular Weight: 409.439

Synonyms:(S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Chemical Property of (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

Chemical Property:

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Technology Process of (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

There total 1 articles about (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-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:

piperonal (120-57-0,30024-74-9) + (4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one (104266-88-8) → (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one (195321-27-8)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, 0 deg C; 2) CH₂Cl₂, 0 deg C, 10 min; 3) CH₂Cl₂, -78 deg C, 30 min, 0 deg C, 1 h;

DOI:10.1021/jo971027c

Reference yield: 100.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one (195321-27-8) → (S)-4-benzyl-3-{(S)-2-[(S)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-pentenoyl}-2-oxazolidinone (1201327-25-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; Cooling with ice;

DOI:10.1271/bbb.90107

Reference yield: 73.0%

(S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one (195321-27-8) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7) + (1S,2R)-2-allyl-1-(3,4-methylenedioxyphenyl)-1,3-propanediol (195321-26-7)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; diethyl ether; water; at 0 ℃; for 1.25h;

DOI:10.1021/jo971027c

upstream raw materials:

piperonal

(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

Downstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

(1S,2R)-2-allyl-1-(3,4-methylenedioxyphenyl)-1,3-propanediol

(1S,2R)-1-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-1-ol

[(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane

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