[(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester
• CAS No.: 882400-16-0
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417
• Mol file: 882400-16-0.mol

Synonyms:[(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

Chemical Property of [(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

There total 1 articles about [(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic 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:

(Z)-(S)-5-Benzyloxycarbonylamino-6-phenyl-hex-3-enoic acid methyl ester → [(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester (882400-16-0) + [(2R,3S)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester

Guidance literature:

With disodium hydrogenphosphate; urea hydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 4h; Further Variations:; Reagents; Product distribution;

DOI:10.1055/s-2005-921907

Reference yield: 65.0%

[(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester (882400-16-0) → (S)-3-((4S,5S)-4-Benzyl-2-oxo-oxazolidin-5-yl)-3-hydroxy-propionic acid methyl ester (882400-18-2)

Guidance literature:

With zirconium(IV) chloride; In dichloromethane; Heating;

DOI:10.1055/s-2005-921907

Reference yield:

[(2S,3R)-3-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-oxiranyl]-acetic acid methyl ester (882400-16-0) → (4R,5S)-5-Amino-4-hydroxy-6-phenyl-hexanoic acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / ZrCl₄ / CH₂Cl₂ / Heating

2: MsCl; Et₃N / CH₂Cl₂

3: NaBH₄; NiCl₂*6H₂O / methanol

4: aq. NaOH / ethanol

With sodium hydroxide; sodium tetrahydroborate; zirconium(IV) chloride; methanesulfonyl chloride; triethylamine; nickel dichloride; In methanol; ethanol; dichloromethane;

DOI:10.1055/s-2005-921907

Downstream raw materials:

(S)-3-((4S,5S)-4-Benzyl-2-oxo-oxazolidin-5-yl)-3-hydroxy-propionic acid methyl ester

(E)-(4S,5S)-5-Benzyloxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester

3-((4S,5R)-4-Benzyl-2-oxo-oxazolidin-5-yl)-propionic acid methyl ester

phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate