(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 399559-48-9
• Molecular Formula: C₂₁H₃₁NO₅S
• Molecular Weight: 409.547

Synonyms:(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + (SS)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene (261900-93-0) → (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (399559-48-9) + (S)-4-[(S)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:

With sodium iodide; zinc(II) chloride; zinc; ammonium chloride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo016068u

Reference yield: 91.0%

(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (399559-48-9) → (2S,3R,RS)-2-amino-5-[(4-methylphenyl)sulfinyl]-5-hexene-1,3-diol

Guidance literature:

With acetyl chloride; In methanol; at 5 - 20 ℃; for 8h;

DOI:10.1002/1099-0690(200301)2003:1<217::AID-EJOC217>3.0.CO;2-W

Reference yield: 85.0%

(S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (399559-48-9) → tert-butyl (1'S,2'R,RS)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate (505085-60-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 3h;

DOI:10.1002/1099-0690(200301)2003:1<217::AID-EJOC217>3.0.CO;2-W

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene

Downstream raw materials:

tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate

tert-butyl (4R,5S,R_S)-2,2-dimethyl-4-{2-[(4-methylphenyl)sulfinyl]-2-propenyl}-1,3-dioxan-5-ylcarbamate

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