(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

Base Information

Chemical Name:(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde
CAS No.:625123-47-9
Molecular Formula:C₂₆H₃₄N₂O₇Si
Molecular Weight:514.651
Hs Code.:

Synonyms:(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

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Chemical Property of (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

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Technology Process of (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

There total 6 articles about (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde 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: 70.0%

: 625123-46-8
methyl (2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxylate

: 625123-47-9
(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/j.bmcl.2003.08.071

Reference yield:

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

: 625123-47-9
(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 60547-92-4
4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

: 625123-47-9
(2S,4R)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(t-butyldimethylsilyl)-oxypyrrolidine-2-carboxaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: thionyl chloride; DMF / benzene / 6 h

2: 75 percent / triethylamine / tetrahydrofuran; H₂O / 1 h / 20 °C

3: 90 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

4: 65 percent / diisobutyl aluminium hydride / hexane; CH₂Cl₂ / 0.75 h / -78 °C

With 1H-imidazole; thionyl chloride; diisobutylaluminium hydride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; water; benzene;
DOI:10.1016/j.bmc.2004.06.013