2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Base Information

Chemical Name:2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester
CAS No.:65750-53-0
Molecular Formula:C₄₂H₃₈N₆O₁₈S
Molecular Weight:946.859
Hs Code.:

2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Synonyms:2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

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Technology Process of 2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

There total 11 articles about 2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) 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: 69.0%

: 65750-60-9
2-Chloro-2-{(2S,3S)-2-{(E)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

: 65750-53-0
2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Guidance literature:: With dipotassium hydrogenphosphate; tributylphosphine; In water; N,N-dimethyl-formamide; for 0.583333h;
DOI:10.1021/jo01294a044

Reference yield:

: 65750-59-6
2-(4-nitrobenzyloxycarbonylamino)ethanethiol

: 65750-53-0
2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Guidance literature:: Multi-step reaction with 5 steps

1: BF₃*Et₂O / acetonitrile / 3 h / 0 °C

2: 1.) Br₂; 2.) Et₃N / 1.) pentane, THF, ether, 0 deg C, 10 min; 2.) cyclohexene; 3.) Et₃N, DMF, r.t. 2 h

3: 41 percent / tetrahydrofuran; toluene / 2.5 h / Heating

4: SOCl₂/pyridine / tetrahydrofuran / 1.) 5 min, -20 deg C; 2.) 0.5 h, 0 deg C; 3.) 1 h, 25 deg C

5: 69 percent / Bu₃P, K₂HPO₄ / dimethylformamide; H₂O / 0.58 h

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo01294a044

Reference yield:

: 65750-58-5
bis(p-nitrobenzyl) ketomalonate

: 65750-53-0
2-{(2S,3S)-2-{(E)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

Guidance literature:: Multi-step reaction with 3 steps

1: 41 percent / tetrahydrofuran; toluene / 2.5 h / Heating

2: SOCl₂/pyridine / tetrahydrofuran / 1.) 5 min, -20 deg C; 2.) 0.5 h, 0 deg C; 3.) 1 h, 25 deg C

3: 69 percent / Bu₃P, K₂HPO₄ / dimethylformamide; H₂O / 0.58 h

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo01294a044