(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:90628-91-4
Molecular Formula:C₂₅H₃₆N₂O₆SSi
Molecular Weight:520.722
Hs Code.:

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Synonyms:(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-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-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-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-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 8 articles about (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-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: 51.0%

: 90628-90-3
C₃₁H₅₁N₂O₁₀PSSi

: 90628-91-4
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: hydroquinone; In xylene; at 120 ℃; for 70h;
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

: 90628-91-4
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-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 / 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: toluene / 80 - 90 °C / 1-3 hrs

8: 51 percent / hydroquinone / xylene / 70 h / 120 °C

With hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; hydroquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene; xylene; 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

: 90628-91-4
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 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: toluene / 80 - 90 °C / 1-3 hrs

5: 51 percent / hydroquinone / xylene / 70 h / 120 °C

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