(2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester
• CAS No.: 186025-79-6
• Molecular Formula: C₁₃H₁₅NO₅
• Molecular Weight: 265.266
• Mol file: 186025-79-6.mol

Synonyms:(2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester

Chemical Property of (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester

There total 3 articles about (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester 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: 43.0%

(E)-3-((R)-2-Phenyl-4,5-dihydro-oxazol-4-yl)-acrylic acid methyl ester (186025-73-0) → (2R,3S)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester (186025-77-4) + (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester (186025-79-6)

Guidance literature:

With osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; for 48h; Ambient temperature;

DOI:10.1021/jo962028s

Reference yield:

ethyl benzimidate hydrochloride (5333-86-8) → (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester (186025-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 1.) reflux, 4 h, 2.) room temperature, overnight

2: 1.) DIBAL-H / 1.) toluene, -78 deg C, 3 h, 2.) toluene, MeOH, room temperature, overnight

3: 27 percent / aq. OsO₄, N-methylmorpholine N-oxide / acetone / 36 h / Ambient temperature

With osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; acetone;

DOI:10.1021/jo962028s

Reference yield:

methyl (S)-2-phenyl-4,5-dihydrooxazole-4-carboxylate (78715-83-0) → (2S,3R)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester (186025-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBAL-H / 1.) toluene, -78 deg C, 3 h, 2.) toluene, MeOH, room temperature, overnight

2: 27 percent / aq. OsO₄, N-methylmorpholine N-oxide / acetone / 36 h / Ambient temperature

With osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In acetone;

DOI:10.1021/jo962028s

upstream raw materials:

(E)-3-((R)-2-Phenyl-4,5-dihydro-oxazol-4-yl)-acrylic acid methyl ester

ethyl benzimidate hydrochloride

methyl (S)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

Downstream raw materials:

Benzoic acid (2S,3R,4S)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester

(2S,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol