(4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone
• CAS No.: 135821-30-6
• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.39
• Mol file: 135821-30-6.mol

Synonyms:(4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone

Chemical Property of (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone

There total 15 articles about (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-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: 90.0%

cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one (110289-27-5) → (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone (135821-30-6)

Guidance literature:

With NaNH₄; In methanol;

DOI:10.1021/jo9612180

Reference yield:

(R)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)acetyl chloride (112674-71-2) → (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone (135821-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) toluene, 0 deg C, 2 h; room temperature, overnight

2: 1.) p-TsOH*H₂O, 2.) NaIO₄ / 1.) THF, H₂O, reflux, 6 h, 2.) Me₂CO, H₂O, 0-5 deg C, 1.5 h

3: 90 percent / NaNH₄ / methanol

With sodium periodate; toluene-4-sulfonic acid; triethylamine; In methanol;

DOI:10.1021/jo9612180

Reference yield:

(S)-4-[(E)-Benzylimino-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (144512-27-6) → (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone (135821-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.)triethylamine / 1.) CH₂Cl₂, toluene, 0 deg C, 2 h, 2.) CH₂Cl₂, toluene, RT, overnight

2: aq. 3 N HCl / methanol / 2 h / Heating

3: NaIO₄ / acetone; H₂O / 24 h / Ambient temperature

4: NaBH₄ / methanol / 0.75 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; triethylamine; In methanol; water; acetone;

DOI:10.1021/ja00050a016

upstream raw materials:

cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one

(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine

(R)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)acetyl chloride

(R)-3-[(2R,3R)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one