[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

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Chemical Name:[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone
CAS No.:642478-88-4
Molecular Formula:C₂₄H₂₉N₅O₅S₂
Molecular Weight:531.657
Hs Code.:

Synonyms:[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

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Chemical Property of [(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

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Technology Process of [(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

There total 6 articles about [(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone 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: 92.0%

: 1006904-31-9
C₂₀H₁₉N₅O₆

: 75-08-1
ethanethiol

: 642478-88-4
[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Guidance literature:: With chloro-trimethyl-silane; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2008.04.006

Reference yield: 76.0%

: 642478-87-3
Methanesulfonic acid (3R,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl ester

: 642478-88-4
[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 16h;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 642478-88-4
[(2S,4S)-4-Azido-2-(bis-ethylsulfanyl-methyl)-pyrrolidin-1-yl]-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-methanone

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / SOCl₂; H₂O / benzene / 2 h / 20 °C

2: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

3: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

5: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

6: 76 percent / NaN₃ / dimethylformamide / 16 h / 60 °C

With 1H-imidazole; chloro-trimethyl-silane; thionyl chloride; sodium azide; TEA; water; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.bmcl.2003.08.071