methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

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Chemical Name:methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate
CAS No.:1315158-66-7
Molecular Formula:C₁₈H₂₃NO₇
Molecular Weight:365.383
Hs Code.:

Synonyms:methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

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Chemical Property of methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

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Technology Process of methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

There total 9 articles about methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate 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: 91.0%

: 1315158-63-4
methyl (4S)-4-[(1'R)-1'-acetoxy-4'-(benzyloxy)butyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

: 1315158-66-7
methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 17h;
DOI:10.2478/s11696-011-0030-5

Reference yield:

: ethyl-3-{(3aR,4'S,5R,6aR)-2,2-dimethyl-2'-oxodihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidine]-5-yl}acrylate

: 1315158-66-7
methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -15 °C / Inert atmosphere

2.2: 2 h / -15 - -5 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 3.16 h / 0 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / water / 5 h / 20 °C / Inert atmosphere

5.1: sodium periodate / methanol; water / 2 h / 20 °C / Inert atmosphere

5.2: 17.16 h / 0 - 20 °C / Inert atmosphere

6.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

7.1: potassium carbonate / methanol / 0.33 h / 0 °C / Inert atmosphere

7.2: Amberlite IR-120 (H⁺) / Inert atmosphere

8.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C

With pyridine; dmap; sodium periodate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.2478/s11696-011-0030-5

Reference yield:

: 1315158-43-0
(3aR,4'S,5R,6aR)-5-(3-hydroxypropyl)-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

: 1315158-66-7
methyl (4S)-4-[(1'R)-1'-acetoxy-4'-hydroxybutyl]-3-benzyl-2-oxooxazolidine-4-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 3.16 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 5 h / 20 °C / Inert atmosphere

3.1: sodium periodate / methanol; water / 2 h / 20 °C / Inert atmosphere

3.2: 17.16 h / 0 - 20 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 0.33 h / 0 °C / Inert atmosphere

5.2: Amberlite IR-120 (H⁺) / Inert atmosphere

6.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C

With pyridine; dmap; sodium periodate; palladium 10% on activated carbon; hydrogen; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.2478/s11696-011-0030-5