(4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone
• CAS No.: 106799-08-0
• Molecular Formula: C₂₁H₂₉NO₆
• Molecular Weight: 391.464
• Mol file: 106799-08-0.mol

Synonyms:(4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property of (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone

There total 2 articles about (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-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:

*R*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol (74243-89-3) → (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone (106799-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / PCC, 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h

2: 1.) n-Bu₂BOTf, i-Pr₂EtN / 1.) CH₂Cl₂, 0 deg C, 0.5 h; 2.) CH₂Cl₂, -78 deg C, 0.5 h; 3.) CH₂Cl₂, roomtemp., 1.5 h

With 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/ja00222a028

Reference yield:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one (77877-20-4) + *S*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde (114925-44-9) → (4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone (106799-08-0)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 0.5 h; 2.) CH₂Cl₂, -78 deg C, 0.5 h; 3.) CH₂Cl₂, roomtemp., 1.5 h;

DOI:10.1021/ja00222a028

Reference yield:

(4R,5S)-3-<2,4-dideoxy-2,4-dimethyl-5,6-O-(methylethylidene)-L-altronoyl>-4-methyl-5-phenyl-2-oxazolidinone (106799-08-0) → 2,4-dideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-dimethyl-6-S-phenyl-6-thio-L-altritol 2,2-dimethylpropanoate

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / LiBH₄ / tetrahydrofuran / 4 h / -40 °C

2: 90 percent / pyridine / 4 h / Ambient temperature

3: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 72 percent / acetic acid, water / tetrahydrofuran / 4.5 h / 45 °C

5: 95 percent / n-Bu₃P / tetrahydrofuran / 6 h / Ambient temperature

With 2,6-dimethylpyridine; lithium borohydride; tributylphosphine; water; acetic acid; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/ja00222a028

upstream raw materials:

(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

*S^*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde

*R^*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol