(R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester

Base Information

• Chemical Name: (R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester
• CAS No.: 157584-72-0
• Molecular Formula: C₃₆H₃₁N₃O₅S₂
• Molecular Weight: 649.791
• Mol file: 157584-72-0.mol

Synonyms:

Chemical Property of (R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester

There total 1 articles about (R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl 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:

diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide (51446-87-8) + 2-sulfanyl-1,3-benzoxazole (2382-96-9,118090-08-7) → (R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester (157584-72-0)

Guidance literature:

In toluene; for 3h; Yield given; Heating;

DOI:10.1021/jo00096a045

Reference yield:

(R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester (157584-72-0) → Diphenylmethyl 2-<(3R,4R)-4-<(benzoxazol-2-yl)dithio>-3-(phenylacetamido)-2-oxoazetidin-1-yl>-3-<(benzoxazol-2-yl)thio>-2-butenoate

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃, 2.) Me₂S / 1.) EtOAc, -78 deg C, 2.) -78 deg C to r.t.

2: i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

3: 45 percent / TEA / CH₂Cl₂ / 3 h / Ambient temperature

With dimethylsulfide; TEA; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00096a045

Reference yield:

(R)-2-[(2R,3R)-2-(Benzooxazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-3-methyl-but-3-enoic acid benzhydryl ester (157584-72-0) → Diphenylmethyl 2-<(3R,4R)-4-<(benzoxazol-2-yl)dithio>-3-(phenylacetamido)-2-oxoazetidin-1-yl>-3-<(trifluorosulfonyl)oxy>-2-butenoate

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S / 1.) EtOAc, -78 deg C, 2.) -78 deg C to r.t.

2: i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

With dimethylsulfide; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00096a045

upstream raw materials:

diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide

2-sulfanyl-1,3-benzoxazole