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

Base Information

Chemical Name:(4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine
CAS No.:135204-37-4
Molecular Formula:C₁₅H₂₁NO₃S
Molecular Weight:295.403
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 6 articles about (4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-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:

: 135204-36-3
(4S,5S)-3-acetyl-2,2-dimethyl-4-formyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine

: 135204-37-4
(4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Guidance literature:: With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 5 ℃; for 2h; Yield given;
DOI:10.1021/jo00021a028

Reference yield:

: 16854-32-3
(1S,2S)-(+)-thiomicamine

: 135204-37-4
(4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 135204-38-5
(4S,5S)-5-(4-methylthiophenyl)-4-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine

: 135204-37-4
(4R,5S)-3-acetyl-2,2-dimethyl-4-(hydroxymethyl)-5-<4-(methylthio)phenyl>-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 3 h / 15 °C

2: K₂CO₃, MeOH / 1 h / 25 °C

3: 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

4: DABCO / 3 h / 35 °C

5: NaBH₄, CaCl₂ / tetrahydrofuran; ethanol / 2 h / 5 °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;
DOI:10.1021/jo00021a028