(4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate

Base Information

• Chemical Name: (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate
• CAS No.: 1374847-26-3
• Molecular Formula: C₂₃H₂₂N₂O₅
• Molecular Weight: 406.438

Synonyms:(4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate

Chemical Property of (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate

Chemical Property:

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Technology Process of (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate

There total 4 articles about (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate 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: 47.0%

indole (120-72-9) + (E)-ethyl 2-acetoxy-3-nitro-4-phenylbut-3-enoate (1268719-97-6,1268720-00-8,1268720-23-5) + acrolein (107-02-8,25068-14-8) → (2R)-ethyl 2-acetoxy-3-nitro-4-phenylbut-(3E)-enoate (1268720-00-8) + (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate (1374847-26-3)

Guidance literature:

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In toluene; at 0 ℃; for 6.5h; optical yield given as %ee; stereoselective reaction; Resolution of racemate;

DOI:10.1021/ol300783e

Reference yield: 47.0%

indole (120-72-9) + (E)-ethyl 2-acetoxy-3-nitro-4-phenylbut-3-enoate (1268719-97-6,1268720-00-8,1268720-23-5) + acrolein (107-02-8,25068-14-8) → (2S)-ethyl 2-acetoxy-3-nitro-4-phenylbut-(3E)-enoate (1268720-23-5) + (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate (1374847-26-3)

Guidance literature:

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In toluene; at 0 ℃; for 7h; Catalytic behavior;

DOI:10.1021/ol503315p

Reference yield:

indole (120-72-9) + (E)-ethyl 2-acetoxy-3-nitro-4-phenylbut-3-enoate (1268719-97-6,1268720-00-8,1268720-23-5) + acrolein (107-02-8,25068-14-8) → (2S)-ethyl 2-acetoxy-3-nitro-4-phenylbut-(3E)-enoate (1268720-23-5) + (2R)-ethyl 2-acetoxy-3-nitro-4-phenylbut-(3E)-enoate (1268720-00-8) + (4S,5R)-ethyl 5-formyl-6-(1H-indol-3-yl)-3-nitro-4-phenylhex-(2E)-enoate (1374847-26-3)

Guidance literature:

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid; In toluene; at 0 ℃; for 6.5h; optical yield given as %ee; stereoselective reaction; Resolution of racemate;

DOI:10.1021/ol300783e

upstream raw materials:

indole

(E)-ethyl 2-acetoxy-3-nitro-4-phenylbut-3-enoate

acrolein

Downstream raw materials:

ethyl 4-(3-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-3-nitro-4-phenylbut-2-enoate

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