6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

Base Information

• Chemical Name: 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester
• CAS No.: 72765-22-1
• Molecular Formula: C₃₄H₂₉N₅O₁₃S
• Molecular Weight: 747.696
• Mol file: 72765-22-1.mol

Synonyms:

Chemical Property of 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

There total 13 articles about 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic 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:

(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (65750-54-1) → 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (72765-22-1) + 6-Eth-(Z)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (72749-11-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 25 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo01294a044

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (72765-22-1)

Guidance literature:

Multi-step reaction with 7 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

6: 1.) Br₂ ; 2.) Et₃N / 1.) pentane, THF/ether, 15 min, 0 deg C; 2.) DMF, 2 h, r.t.

7: DBU / dimethylsulfoxide / 2 h / 25 °C

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; boron trifluoride diethyl etherate; bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo01294a044

Reference yield:

bis(p-nitrobenzyl) ketomalonate (65750-58-5) → 6-Eth-(E)-ylidene-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (72765-22-1)

Guidance literature:

Multi-step reaction with 5 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

4: 1.) Br₂ ; 2.) Et₃N / 1.) pentane, THF/ether, 15 min, 0 deg C; 2.) DMF, 2 h, r.t.

5: DBU / dimethylsulfoxide / 2 h / 25 °C

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo01294a044

upstream raw materials:

(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

bis(p-nitrobenzyl) ketomalonate

Bis(p-nitrobenzyl) malonate