(3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-2-azetidinone
• CAS No.: 90694-08-9
• Molecular Formula: C₂₁H₂₀N₂O₇S
• Molecular Weight: 444.465

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

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

Chemical Property:

Purity/Quality:

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

There total 20 articles about (3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-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: 93.0%

phenyl thiolester (90628-92-5) + Acetic acid (2R,3R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester (97033-08-4) → (3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-2-azetidinone (90694-08-9)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 25h; Mechanism; Ambient temperature;

DOI:10.1016/S0040-4039(00)89176-5

Reference yield: 90.0%

((1-(phenylthio)vinyl)oxy)trimethylsilane (80675-54-3) + Acetic acid (2R,3R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester (97033-08-4) → (3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-2-azetidinone (90694-08-9)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 25h; Mechanism;

DOI:10.1016/S0040-4039(00)89176-5

Reference yield: 70.0%

(3S,4R)-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone (90629-24-6) → (3S,4R)-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-4-<(phenylthiocarbonyl)methyl>-2-azetidinone (90694-08-9)

Guidance literature:

With ammonium cerium(IV) nitrate;

DOI:10.1016/S0040-4039(00)88946-7

upstream raw materials:

((1-(phenylthio)vinyl)oxy)trimethylsilane

Acetic acid (2R,3R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester

phenyl thiolester

(3S,4R)-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Downstream raw materials:

(3S,4R)-4-<<2-(p-nitrobenzyloxycarbonylamino)etylthio>carbonylmethyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

{(3S,4R)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-phenylsulfanylcarbonylmethyl-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

(+/-)-p-nitrobenzyl 6α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(+/-)-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-1--4β-<(phenylthio)carbonylmethyl>azetidin-2-one

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