(4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester
• CAS No.: 187157-78-4
• Molecular Formula: C₃₃H₂₉N₅O₄
• Molecular Weight: 559.624

Synonyms:(4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester

Chemical Property of (4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester

There total 7 articles about (4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl 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: 90.0%

(4S,5S)-1-Benzyl-5-((S)-2-chloro-1-hydroxy-ethyl)-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid methyl ester (187157-76-2) → (4S,5S,1IVR)-1-benzyl-5-(1IV-hydroxy-2IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester (187157-78-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 110 ℃; for 6.5h;

DOI:10.1021/jo970277q

Reference yield:

dimethyl (2S,3S)-2-azido-3-(9-phenyl-9H-fluoren-9-ylamino)succinate (159434-59-0) → (4S,5S,1IVR)-1-benzyl-5-(1IV-hydroxy-2IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester (187157-78-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂, 2.) Na₂CO₃ / 1.) Pd/BaCO₃ / 1.) MeOH, 1 atm, 3 h, 2.) CH₂Cl₂, H₂O, reflux, 54 h

2: 83 percent / DMAP / pyridine / 0.33 h / 70 °C

3: 100 percent / MeLi, LiBr / tetrahydrofuran; diethyl ether / 1.25 h / -78 °C

4: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

5: 90 percent / NaN₃ / dimethylformamide / 6.5 h / 110 °C

With dmap; sodium azide; methyllithium; hydrogen; diisobutylaluminium hydride; sodium carbonate; lithium bromide; palladium-barium carbonate; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo970277q

Reference yield:

benzyl bromide (100-39-0) → (4S,5S,1IVR)-1-benzyl-5-(1IV-hydroxy-2IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester (187157-78-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂, 2.) Na₂CO₃ / 1.) Pd/BaCO₃ / 1.) MeOH, 1 atm, 3 h, 2.) CH₂Cl₂, H₂O, reflux, 54 h

2: 83 percent / DMAP / pyridine / 0.33 h / 70 °C

3: 100 percent / MeLi, LiBr / tetrahydrofuran; diethyl ether / 1.25 h / -78 °C

4: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

5: 90 percent / NaN₃ / dimethylformamide / 6.5 h / 110 °C

With dmap; sodium azide; methyllithium; hydrogen; diisobutylaluminium hydride; sodium carbonate; lithium bromide; palladium-barium carbonate; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo970277q

upstream raw materials:

(4S,5S)-1-Benzyl-5-((S)-2-chloro-1-hydroxy-ethyl)-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid methyl ester

benzyl bromide

dimethyl (2S,3S)-2-azido-3-(9-phenyl-9H-fluoren-9-ylamino)succinate

(2S,3S)-2-Benzylamino-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester

Downstream raw materials:

(4S,5S)-5-((R)-2-Azido-1-hydroxy-ethyl)-1-benzyl-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid

(3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione

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