(S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester
• CAS No.: 223763-56-2
• Molecular Formula: C₂₁H₃₀N₂O₅
• Molecular Weight: 390.48
• Mol file: 223763-56-2.mol

Synonyms:(S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

Chemical Property of (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

There total 2 articles about (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic 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:

(4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one (95832-37-4) → (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester (223763-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaIO₄ / RuCl₃*xH₂O / CCl₄; acetonitrile; H₂O / 15.5 h / Ambient temperature

2: i-Pr₂NEt, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) / acetonitrile / 21.5 h / Ambient temperature

With sodium periodate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; ruthenium trichloride; In tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo9823893

Reference yield:

(4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one (223763-61-9) → (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester (223763-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

2: NaIO₄ / RuCl₃*xH₂O / CCl₄; acetonitrile; H₂O / 15.5 h / Ambient temperature

3: i-Pr₂NEt, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) / acetonitrile / 21.5 h / Ambient temperature

With sodium periodate; tetrabutyl ammonium fluoride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo9823893

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester (223763-56-2) → 4-benzyl-5-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (223763-70-0)

Guidance literature:

With dmap; In tetrahydrofuran; for 21.5h; Ambient temperature;

DOI:10.1021/jo9823893

upstream raw materials:

(4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one

(4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one

Downstream raw materials:

4-benzyl-5-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

2-(3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid tert-butyl ester

bestatin trifluroacetate salt