[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate

Base Information

• Chemical Name: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate
• CAS No.: 138511-90-7
• Molecular Formula: C₁₁H₁₂F₂O₄S
• Molecular Weight: 278.277

Synonyms:[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate

Chemical Property of [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate

Chemical Property:

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Technology Process of [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate

There total 13 articles about [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate 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: 100.0%

(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol (126918-33-0) + methanesulfonyl chloride (124-63-0) → [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate (138511-90-7)

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃; for 0.166667h;

DOI:10.1248/cpb.39.2241

Reference yield:

(2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol (126918-32-9) → [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate (138511-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / tert-butyl hydroperoxide; L-(+)-diethyl tartrate; titanium(IV) isopropoxide / CH₂Cl₂; toluene / 8 h / -20 - -10 °C

2: triethylamine / CH₂Cl₂ / 1 h / 5 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; triethylamine; In dichloromethane; toluene; 1: Sharpless stereoselective epoxidation;

DOI:10.1016/j.bmc.2004.02.014

Reference yield:

(2R*,3R*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol (126918-21-6,132563-68-9) → Methanesulfonic acid (S)-1-[(R)-2-(2,4-difluoro-phenyl)-oxiranyl]-ethyl ester (126918-36-3,132563-69-0,135270-14-3,138511-90-7)

Guidance literature:

With sodium 1,2,3-triazolate; In N,N-dimethyl-formamide; at 65 - 70 ℃; for 0.25h; Yield given;

DOI:10.1248/cpb.38.2476

upstream raw materials:

(2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol

(2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol

1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one

(2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol

Downstream raw materials:

(2S,3R)-2-(2,4-difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane

1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole

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