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

Base Information

Chemical Name:(5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester
CAS No.:65794-43-6
Molecular Formula:C₄₂H₃₆N₆O₁₈S
Molecular Weight:944.843
Hs Code.:

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

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

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

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

There total 26 articles about (5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-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: 79.0%

: 65750-54-1
(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

: 65750-55-2,65794-43-6
(5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[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

Guidance literature:: With silver fluoride; In pyridine; for 1h;
DOI:10.1021/jo01294a044

Reference yield:

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

: 65794-43-6
(5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(S)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

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: 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: 0.021 g / AgF / pyridine / 1 h

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

Reference yield:

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

: 65750-55-2,65794-43-6
(5R,6R)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[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

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: 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: 79 percent / AgF / pyridine / 1 h

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