(4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Base Information

• Chemical Name: (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine
• CAS No.: 135204-55-6
• Molecular Formula: C₁₇H₂₃NO₄S
• Molecular Weight: 337.44
• Mol file: 135204-55-6.mol

Synonyms:(4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Chemical Property of (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

There total 10 articles about (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine 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)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine (135204-37-4) + acetyl chloride (75-36-5) → (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine (135204-55-6)

Guidance literature:

With triethylamine; In dichloromethane; at 15 ℃; for 1h; Yield given;

DOI:10.1021/jo00021a028

Reference yield:

(4S,5S)-5-(4-methylthiophenyl)-4-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine (135204-38-5) + acetyl chloride (75-36-5) → (4S,5S)-5-(4-methylthiophenyl)-4-acetoxymethyl-3-acetyl-2,2-dimethyl-1,3-oxazolidine (135204-33-0,135204-55-6,135761-13-6)

Guidance literature:

With triethylamine; In dichloromethane; at 15 ℃; for 3h;

DOI:10.1021/jo00021a028

Reference yield:

(1S,2S)-(+)-thiomicamine (16854-32-3) → (4R,5S)-4-(acetoxymethyl)-3-acetyl-2,2-dimethyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine (135204-55-6)

Guidance literature:

Multi-step reaction with 7 steps

1: toluene / 18 h / Heating

2: Et₃N / CH₂Cl₂ / 3 h / 15 °C

3: K₂CO₃, MeOH / 1 h / 25 °C

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, a) -60 deg C, 15 min, b) up to -50 deg C, 2) a) -50 deg C, 20 min, b) up to 0 deg C, 2 h

5: DABCO / 3 h / 35 °C

6: NaBH₄, CaCl₂ / tetrahydrofuran; ethanol / 2 h / 5 °C

7: Et₃N / CH₂Cl₂ / 1 h / 15 °C

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; sodium tetrahydroborate; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo00021a028

upstream raw materials:

(4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine

acetyl chloride

(1S,2S)-(+)-thiomicamine

(4S,5S)-5-(4-methylthiophenyl)-4-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine

Downstream raw materials:

Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid

(R*,R*)-(+)-thiomicamine

(+)-(1S,2R)-2-amino-1-<4-(methylthio)phenyl>-1,3-propanediol

(4S,5S)-3-acetyl-2,2-dimethyl-4-formyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine