(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone
CAS No.:90629-07-5
Molecular Formula:C₂₇H₂₈N₄O₁₁S
Molecular Weight:616.606
Hs Code.:

Synonyms:(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

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Chemical Property of (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

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Technology Process of (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

There total 7 articles about (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone 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: 87.0%

: 90629-00-8
(S)-3-(2-Trimethylsilanyl-acetylsulfanyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 97033-08-4
Acetic acid (2R,3R)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester

: 90629-07-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

Guidance literature:: trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 28h; Mechanism; Ambient temperature;
DOI:10.1016/S0040-4039(00)89176-5

Reference yield: 61.0%

: 92133-38-5
(S)-3-{2-[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 4457-32-3
4-nitrobenzyl chloroformate

: 90629-07-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

Guidance literature:: With dmap; In dichloromethane;
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

: 90629-07-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 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

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