(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Base Information

Chemical Name:(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone
CAS No.:72888-48-3
Molecular Formula:C₁₅H₁₆N₂O₈
Molecular Weight:352.301
Hs Code.:

Synonyms:(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

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Chemical Property of (3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

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Technology Process of (3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

There total 10 articles about (3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone 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: 94.0%

: 91603-19-9
(3R,4R)-4-acetoxy-1-(di-p-anisylmethyl)-3-<(R)-1-p-nitrobenzyloxycarbonyloxyethyl>-2-azetidinone

: 72888-48-3
(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: With ammonium cerium(IV) nitrate; In methanol; water; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.39.1931

Reference yield:

: 96035-87-9
(2S,3R)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carbonyl chloride

: 72888-48-3
(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

2: 74 percent / 1 N NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

3: 75 percent / AcOK / dimethylformamide / 1 h / Ambient temperature

4: 1.) mercuric acetate, water 2.) 1 N NaOH, NaBH₄ / 1.) THF, 25 deg C 2.) 25 deg C

5: 90 percent / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

6: 94 percent / ceric(IV) ammonium nitrate / H₂O; methanol / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; ammonium cerium(IV) nitrate; mercury(II) diacetate; water; potassium acetate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.1931

Reference yield:

: 86207-15-0,138008-06-7
(3RS,4RS)-4-n-butoxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone

: 72888-48-3
(3R,4R)-4-acetoxy-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / 1 N NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

2: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1.5 h / Ambient temperature

3: Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4: 74 percent / 1 N NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

5: 75 percent / AcOK / dimethylformamide / 1 h / Ambient temperature

6: 1.) mercuric acetate, water 2.) 1 N NaOH, NaBH₄ / 1.) THF, 25 deg C 2.) 25 deg C

7: 90 percent / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

8: 94 percent / ceric(IV) ammonium nitrate / H₂O; methanol / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; mercury(II) diacetate; water; potassium acetate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.1931