2-Hydroxy-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-Hydroxy-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.: 65750-61-0
• Molecular Formula: C₄₂H₃₈N₆O₁₉S
• Molecular Weight: 962.859
• Mol file: 65750-61-0.mol

Synonyms:

Chemical Property of 2-Hydroxy-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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Hydroxy-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 24 articles about 2-Hydroxy-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:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → 2-Hydroxy-2-{(2S,3S)-2-{(E)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester (65750-61-0)

Guidance literature:

Multi-step reaction with 3 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: 26 percent / tetrahydrofuran; toluene / 2.5 h / Heating

With boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1021/jo01294a044

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → 2-Hydroxy-2-{(2S,3S)-2-{(Z)-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 (65750-61-0,65831-09-6,67245-84-5,72843-07-3)

Guidance literature:

Multi-step reaction with 3 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: tetrahydrofuran; toluene / 2.5 h / Heating

With boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1021/jo01294a044

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → 2-Hydroxy-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 (65750-61-0,65831-09-6,67245-84-5,72843-07-3)

Guidance literature:

Multi-step reaction with 3 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

With boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1021/jo01294a044

upstream raw materials:

bis(p-nitrobenzyl) ketomalonate

Carbonic acid 4-nitro-benzyl ester 1-((2R,3R)-2-{(E)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-4-oxo-azetidin-3-yl)-ethyl ester

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

Bis(p-nitrobenzyl) malonate

Downstream raw materials:

(2S,5S,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

(2S,5S,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester