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

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Chemical Name:Methanesulfonic acid (3R,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl ester
CAS No.:642478-87-3
Molecular Formula:C₂₅H₃₂N₂O₈S₃
Molecular Weight:584.736
Hs Code.:

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

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Chemical Property of Methanesulfonic acid (3R,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl ester

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Technology Process of Methanesulfonic acid (3R,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl ester

There total 5 articles about Methanesulfonic acid (3R,5S)-1-(4-benzyloxy-5-methoxy-2-nitro-benzoyl)-5-(bis-ethylsulfanyl-methyl)-pyrrolidin-3-yl 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: 78.0%

: 124-63-0
methanesulfonyl chloride

: 625123-48-0
(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxaldehyde diethyl thioacetal

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

Guidance literature:: With TEA; In dichloromethane; at 0 ℃; for 5h;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 382137-65-7
methyl-(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-hydroxypyrrolidine-2-carboxylate

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

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

2: 70 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

3: 62 percent / TMSCl / CH₂Cl₂ / 8 h / 20 °C

4: 78 percent / TEA / CH₂Cl₂ / 5 h / 0 °C

With 1H-imidazole; chloro-trimethyl-silane; TEA; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/j.bmcl.2003.08.071