(R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 212330-23-9
• Molecular Formula: C₂₀H₂₈N₂O₄
• Molecular Weight: 360.453

Synonyms:(R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-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:

(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide (158723-45-6,188965-45-9) → (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (212330-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / tetrahydrofuran / 0.25 h / -80 °C

2: 88 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo9714775

Reference yield: 100.0%

acetic anhydride (108-24-7) + (R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (212330-23-9) → (3S,4R)-3-(N-acetoxy-N-benzylamino)-5-hydroxy-4,5-N,O-isopropylidene-4-[(tert-butoxycarbonyl)amino]-1-pentyne (212330-24-0)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo9714775

Reference yield: 94.0%

(R)-4-[(S)-1-(Benzyl-hydroxy-amino)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (212330-23-9) → [(1R,2S)-2-(Benzyl-hydroxy-amino)-1-hydroxymethyl-but-3-ynyl]-carbamic acid tert-butyl ester (212330-26-2)

Guidance literature:

With toluene-4-sulfonic acid; In water; Heating;

DOI:10.1021/jo9714775

upstream raw materials:

(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide

Downstream raw materials:

(3S,4R)-3-(N-acetoxy-N-benzylamino)-5-hydroxy-4,5-N,O-isopropylidene-4-[(tert-butoxycarbonyl)amino]-1-pentyne

[(1R,2S)-2-(Benzyl-hydroxy-amino)-1-hydroxymethyl-but-3-ynyl]-carbamic acid tert-butyl ester

(3S,4R)-5-acetoxy-3-(N-acetoxy-N-benzylamino)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-1-pentyne

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