(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:90581-68-3
Molecular Formula:C₃₀H₃₁N₅O₁₀S
Molecular Weight:653.67
Hs Code.:

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 11 articles about (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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: 80.0%

: 98167-74-9
(5R,6S)-3-((S)-1-{1-[(E)-4-Nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-6-((R)-1-trimethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 90581-68-3
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: pyridinium p-toluenesulfonate; In tetrahydrofuran; water;
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

: 90581-68-3
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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 11 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: Et₃N / CH₂Cl₂ / 0 °C

7: boron trifluoride etherate / acetonitrile

8: 90 percent / DMAP / tetrahydrofuran

9: toluene / 80 - 90 °C / 1-3 hrs

10: 63 percent / hydroquinone / toluene / 50 h / 105 °C

11: 80 percent / PPTS / tetrahydrofuran; H₂O

With 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

: 90581-68-3
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-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 8 steps

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

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

3: Et₃N / CH₂Cl₂ / 0 °C

4: boron trifluoride etherate / acetonitrile

5: 90 percent / DMAP / tetrahydrofuran

6: toluene / 80 - 90 °C / 1-3 hrs

7: 63 percent / hydroquinone / toluene / 50 h / 105 °C

8: 80 percent / PPTS / tetrahydrofuran; H₂O

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