(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

Chemical Name:(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal
CAS No.:757189-92-7
Molecular Formula:C₂₇H₃₂N₂O₇S₂
Molecular Weight:560.692
Hs Code.:

Synonyms:(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

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Chemical Property of (2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

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Technology Process of (2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 7 articles about (2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 85.0%

: 1067-74-9
Methyl diethylphosphonoacetate

: 625123-49-1
(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-oxopyrrolidine-2-carboxaldehyde diethyl thioacetal

: 757189-92-7
(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1016/S0960-894X(03)00718-2

Reference yield:

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

: 757189-92-7
(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: Multi-step reaction with 7 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

5: 72 percent / trimethylsilyl chloride / CHCl₃ / 18.5 h

6: 78 percent / TPAP; NMO; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 2.5 h / 20 °C

7: 80 percent / sodium hydride / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; chloro-trimethyl-silane; thionyl chloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetonitrile; benzene;
DOI:10.1016/j.bmc.2004.06.013

Reference yield:

: 64154-78-5
4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

: 757189-92-7
(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]-4-(methoxycarbonylmethylidene)-pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: Multi-step reaction with 6 steps

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

2: 90 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

3: 65 percent / diisobutyl aluminium hydride / hexane; CH₂Cl₂ / 0.75 h / -78 °C

4: 72 percent / trimethylsilyl chloride / CHCl₃ / 18.5 h

5: 78 percent / TPAP; NMO; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 2.5 h / 20 °C

6: 80 percent / sodium hydride / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1016/j.bmc.2004.06.013