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

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Chemical Name:(5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:90629-09-7
Molecular Formula:C₃₆H₃₃N₅O₁₄S
Molecular Weight:791.749
Hs Code.:

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

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

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Chemical Property of (5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 10 articles about (5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-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: 57.0%

: 90629-52-0,92217-94-2
C₄₂H₄₈N₅O₁₈PS

: 90629-09-7
(5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: hydroquinone; In toluene; at 100 ℃; for 80h;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 90629-09-7
(5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature; overnight

3: 91 percent / pyridinium p-toluenesulfonate / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

4: 100 percent / H₂ / 10percent Pd-C / methanol

5: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

6: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

7: 61 percent / DMAP / CH₂Cl₂

8: Et₃N / CH₂Cl₂ / 0 °C

9: toluene / 80 - 90 °C / 1-3 hrs

10: 57 percent / hydroquinone / toluene / 80 h / 100 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; hydroquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 87392-18-5
<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

: 90629-09-7
(5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / H₂ / 10percent Pd-C / methanol

2: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

3: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

4: 61 percent / DMAP / CH₂Cl₂

5: Et₃N / CH₂Cl₂ / 0 °C

6: toluene / 80 - 90 °C / 1-3 hrs

7: 57 percent / hydroquinone / toluene / 80 h / 100 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; hydroquinone; In methanol; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)81292-2