(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

Base Information

• Chemical Name: (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
• CAS No.: 72778-06-4
• Molecular Formula: C₃₄H₃₁N₅O₁₄S
• Molecular Weight: 765.711
• Mol file: 72778-06-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 22 articles about (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 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: 45.0%

(5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester (65750-55-2) → (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 (72778-06-4)

Guidance literature:

With lithium iodide; In various solvent(s); at 120 - 130 ℃; for 0.5h;

DOI:10.1021/jo01294a044

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → (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 (72778-06-4)

Guidance literature:

Multi-step reaction with 8 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

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

5: 57 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: 0.019 g / AgF / pyridine / 1 h

8: 45 percent / LiI / various solvent(s) / 0.5 h / 120 - 130 °C

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; boron trifluoride diethyl etherate; bromine; silver fluoride; triethylamine; lithium iodide; In tetrahydrofuran; pyridine; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo01294a044

Reference yield:

bis(p-nitrobenzyl) ketomalonate (65750-58-5) → (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 (72778-06-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 26 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: 57 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: 0.019 g / AgF / pyridine / 1 h

6: 45 percent / LiI / various solvent(s) / 0.5 h / 120 - 130 °C

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; bromine; silver fluoride; triethylamine; lithium iodide; In tetrahydrofuran; pyridine; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo01294a044

upstream raw materials:

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

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

bis(p-nitrobenzyl) ketomalonate

Bis(p-nitrobenzyl) malonate

Downstream raw materials:

(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