p-nitrobenzyl (+/-)-cis-3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (+/-)-cis-3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 67576-51-6
• Molecular Formula: C₃₄H₃₁N₅O₁₄S
• Molecular Weight: 765.711

Synonyms:

Chemical Property of p-nitrobenzyl (+/-)-cis-3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (+/-)-cis-3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 53 articles about p-nitrobenzyl (+/-)-cis-3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 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: 51.0%

(3S,4R)-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonylmethyl)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-2-azetidinone → (+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (65991-26-6,67576-51-6,72778-09-7,79299-27-7,92217-98-6,106758-28-5)

Guidance literature:

With hydroquinone; In 5,5-dimethyl-1,3-cyclohexadiene; chloroform; ethyl acetate;

Reference yield: 41.5%

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) + (5R,6S)-3-(Diphenoxy-phosphoryloxy)-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 (78072-36-3,96093-91-3,96093-95-7) → (+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (65991-26-6,67576-51-6,72778-09-7,79299-27-7,92217-98-6,106758-28-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -15 ℃; for 20h;

DOI:10.1039/P19810000964

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → (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 (67576-51-6)

Guidance literature:

Multi-step reaction with 9 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

9: diisopropylamine / dimethylsulfoxide / 2 h

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

DOI:10.1021/jo01294a044

upstream raw materials:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-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

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine

magnesium 4-nitrobenzyl malonate

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