(4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone

Base Information

• Chemical Name: (4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone
• CAS No.: 184178-78-7
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 184178-78-7.mol

Synonyms:(4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone

Chemical Property of (4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone

There total 1 articles about (4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone 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:

acetaldehyde (75-07-0,9002-91-9) + (R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0,141423-22-5,141423-21-4) → (4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone (184178-78-7)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine; at -78 ℃;

DOI:10.1021/ja963002l

Reference yield: 100.0%

(4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone (184178-78-7) → (4R)-4-benzyl-3-((2R,3S,4S,5R)-3,5-dihydroxy-2,4-dimethyl-1-oxohexyl)-2-oxazolidinone (211187-45-0)

Guidance literature:

With sodium tetrahydroborate; acetic acid; for 0.25h; Ambient temperature;

DOI:10.1021/ja9806128

Reference yield:

(4R)-4-benzyl-3-((2R,4S,5R)-5-hydroxy-2,4-dimethyl-1,3-dioxohexyl)-2-oxazolidinone (184178-78-7) → (R)-4-Benzyl-3-((2R,3S,4R,5R)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexanoyl)-oxazolidin-2-one (183960-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaBH₄, AcOH / 0.25 h / Ambient temperature

2: 73 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; acetic acid; In dichloromethane;

DOI:10.1021/ja9806128

upstream raw materials:

acetaldehyde

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

Downstream raw materials:

(4R)-4-benzyl-3-((2R,3S,4S,5R)-3,5-dihydroxy-2,4-dimethyl-1-oxohexyl)-2-oxazolidinone

(R)-4-Benzyl-3-((2R,3S,4R,5R)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexanoyl)-oxazolidin-2-one

(R)-4-Benzyl-3-((2R,3S,4S,5R)-2,4-dimethyl-3-triethylsilanyloxy-5-triisopropylsilanyloxy-hexanoyl)-oxazolidin-2-one

(R)-2-[(2S,4S,5R,6S)-6-((S)-2-{(R)-2-[(1S,2R,3S,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-hexyl]-oxiranyl}-1-methyl-ethyl)-5-methyl-2-phenyl-[1,3]dioxan-4-yl]-propionic acid