(R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate
• CAS No.: 104392-60-1
• Molecular Formula: C₁₇H₁₇NO₅S
• Molecular Weight: 347.392
• Mol file: 104392-60-1.mol

Synonyms:(R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate

Chemical Property of (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate

There total 7 articles about (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate 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: 93.0%

(R)-glycidyl tosylate (113826-06-5,6746-81-2) + phenyl isocyanate (103-71-9) → 5-iodomethyl-3-phenyloxazolidin-2-one + 5-iodomethyl-3-phenyloxazolidin-2-one + (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate (104392-60-1)

Guidance literature:

With lithium iodide; In tetrahydrofuran; optical yield given as %ee; regioselective reaction; Reflux;

DOI:10.5012/bkcs.2011.32.12.4450

Reference yield: 87.0%

p-toluenesulfonyl chloride (98-59-9) + (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine (87508-42-7) → (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate (104392-60-1)

Guidance literature:

With pyridine; at 15 ℃;

DOI:10.1021/jm00128a003

Reference yield:

(R)-3-tosyloxy-1,2-propanediol (41274-09-3) + phenyl isocyanate (103-71-9) → (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate (104392-60-1) + (R)-5-(chloromethyl)-3-phenyloxazolidin-2-one

Guidance literature:

(R)-3-tosyloxy-1,2-propanediol; With PS(polymer)-TsCl; triethylamine; In dichloromethane; at 20 ℃;

phenyl isocyanate; With triethylamine; In dichloromethane; at 20 ℃;

With 2,6-dichloro-benzonitrile; In dichloromethane; at 20 ℃; for 2h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ol015723h

upstream raw materials:

p-toluenesulfonyl chloride

(R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine

(R)-3-tosyloxy-1,2-propanediol

phenyl isocyanate

Downstream raw materials:

(R)-5-(fluoromethyl)-3-phenyl-2-oxooxazolidine

(R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide

(S)-N-<<3-<4-(chlorosulfonyl)phenyl>2-oxo-5-oxazolidinyl>methyl> acetamide

(S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide