D-Proline, 4-(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-1-[2-[[(4 -nitrophenyl)sulfonyl]amino]ethyl]-, diphenylmethyl ester, (4R)-

Base Information

• Chemical Name: D-Proline, 4-(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-1-[2-[[(4 -nitrophenyl)sulfonyl]amino]ethyl]-, diphenylmethyl ester, (4R)-
• CAS No.: 318515-54-7
• Molecular Formula: C₃₈H₃₅N₅O₉S
• Molecular Weight: 737.79
• Mol file: 318515-54-7.mol

Synonyms:

Chemical Property of D-Proline, 4-(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-1-[2-[[(4 -nitrophenyl)sulfonyl]amino]ethyl]-, diphenylmethyl ester, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Proline, 4-(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-1-[2-[[(4 -nitrophenyl)sulfonyl]amino]ethyl]-, diphenylmethyl ester, (4R)-

There total 2 articles about D-Proline, 4-(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-1-[2-[[(4 -nitrophenyl)sulfonyl]amino]ethyl]-, diphenylmethyl ester, (4R)- 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:

1-(4-nitro-benzenesulfonyl)-aziridine (43090-97-7) + (2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-2-carboxylic acid benzhydryl ester → (2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-[2-(4-nitro-benzenesulfonylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzhydryl ester (318515-54-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃;

DOI:10.1016/S0960-894X(00)00507-2

Reference yield:

(2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 2-benzhydryl ester 1-tert-butyl ester (189163-50-6) → (2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-[2-(4-nitro-benzenesulfonylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzhydryl ester (318515-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / acetonitrile

2: DIEA / acetonitrile / 20 °C

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In acetonitrile; 1: acidolysis / 2: Ring cleavage;

DOI:10.1016/S0960-894X(00)00507-2

Reference yield:

(2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-[2-(4-nitro-benzenesulfonylamino)-ethyl]-pyrrolidine-2-carboxylic acid benzhydryl ester (318515-54-7) → N-2-(N-tert-butoxycarbonylamino)ethyl-cis-4-(N3-benzoylthymin-1-yl)-D-proline

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; DMAP / CH₂Cl₂

2: PhSH; K₂CO₃ / dimethylformamide / 20 °C

3: 100 percent / cyclohexene / Pd/C / methanol / Heating

With dmap; potassium carbonate; thiophenol; triethylamine; cyclohexene; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: desulfonylation / 3: Hydrogenolysis;

DOI:10.1016/S0960-894X(00)00507-2

upstream raw materials:

1-(4-nitro-benzenesulfonyl)-aziridine

(2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 2-benzhydryl ester 1-tert-butyl ester

Downstream raw materials:

N-2-(N-tert-butoxycarbonylamino)ethyl-cis-4-(N³-benzoylthymin-1-yl)-D-proline diphenylmethyl ester

N-2-(9-fluorenylmethoxycarbonylamino)ethyl-cis-4-(N³-benzoylthymin-1-yl)-D-proline diphenylmethyl ester