L-Phenylalanine, (2R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[4-methoxy-3,5-bis(1-methyleth oxy)phenyl]glycyl-(2R)-2-(4-methoxyphenyl)glycyl-4-fluoro-3-nitro-, methyl ester

Base Information

• Chemical Name: L-Phenylalanine, (2R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[4-methoxy-3,5-bis(1-methyleth oxy)phenyl]glycyl-(2R)-2-(4-methoxyphenyl)glycyl-4-fluoro-3-nitro-, methyl ester
• CAS No.: 178744-42-8
• Molecular Formula: C39H49FN4O12
• Molecular Weight: 784.836
• Mol file: 178744-42-8.mol

Synonyms:

Chemical Property of L-Phenylalanine, (2R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[4-methoxy-3,5-bis(1-methyleth oxy)phenyl]glycyl-(2R)-2-(4-methoxyphenyl)glycyl-4-fluoro-3-nitro-, methyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalanine, (2R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[4-methoxy-3,5-bis(1-methyleth oxy)phenyl]glycyl-(2R)-2-(4-methoxyphenyl)glycyl-4-fluoro-3-nitro-, methyl ester

There total 17 articles about L-Phenylalanine, (2R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[4-methoxy-3,5-bis(1-methyleth oxy)phenyl]glycyl-(2R)-2-(4-methoxyphenyl)glycyl-4-fluoro-3-nitro-, 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:

(3,5-Diisopropoxy-4-methoxy-phenyl)-methanol (918446-55-6) → (S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-diisopropoxy-4-methoxy-phenyl)-acetylamino]-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (178744-42-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / PBr₃ / toluene

2: 97 percent / dimethylsulfoxide

3: 94 percent / K₂CO₃, H₂O₂ / dimethylsulfoxide

4: 88 percent / KOH / ethane-1,2-diol

5: 1.) Me₃CCOCl, Et₃N / 1.) THF

6: 1.) KHDMS, trisyl-N₃, 2.) NaI, NaOAc / 1.) THF, 2.) Me₂SO

7: H₂ / 10percent Pd/C

8: ethyl acetate

9: 90 percent / aq. LiOH / tetrahydrofuran

10: EDC, HOBt, Et₃N / CH₂Cl₂

With potassium hydroxide; lithium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; sodium acetate; pivaloyl chloride; phosphorus tribromide; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethylene glycol; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1039/cc9960001029

Reference yield:

4-methoxy-3,5-diisopropyloxybenzaldehyde (171738-31-1) → (S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-diisopropoxy-4-methoxy-phenyl)-acetylamino]-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (178744-42-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 92 percent / NaBH₄ / ethanol

2: 90 percent / PBr₃ / toluene

3: 97 percent / dimethylsulfoxide

4: 94 percent / K₂CO₃, H₂O₂ / dimethylsulfoxide

5: 88 percent / KOH / ethane-1,2-diol

6: 1.) Me₃CCOCl, Et₃N / 1.) THF

7: 1.) KHDMS, trisyl-N₃, 2.) NaI, NaOAc / 1.) THF, 2.) Me₂SO

8: H₂ / 10percent Pd/C

9: ethyl acetate

10: 90 percent / aq. LiOH / tetrahydrofuran

11: EDC, HOBt, Et₃N / CH₂Cl₂

With potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; sodium acetate; pivaloyl chloride; phosphorus tribromide; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethylene glycol; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1039/cc9960001029

Reference yield:

5-Bromomethyl-1,3-diisopropoxy-2-methoxy-benzene (918446-56-7) → (S)-2-[(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-diisopropoxy-4-methoxy-phenyl)-acetylamino]-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (178744-42-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / dimethylsulfoxide

2: 94 percent / K₂CO₃, H₂O₂ / dimethylsulfoxide

3: 88 percent / KOH / ethane-1,2-diol

4: 1.) Me₃CCOCl, Et₃N / 1.) THF

5: 1.) KHDMS, trisyl-N₃, 2.) NaI, NaOAc / 1.) THF, 2.) Me₂SO

6: H₂ / 10percent Pd/C

7: ethyl acetate

8: 90 percent / aq. LiOH / tetrahydrofuran

9: EDC, HOBt, Et₃N / CH₂Cl₂

With potassium hydroxide; lithium hydroxide; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; sodium acetate; pivaloyl chloride; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethylene glycol; dimethyl sulfoxide; ethyl acetate;

DOI:10.1039/cc9960001029

upstream raw materials:

(R)-N-(t-butoxycarbonyl)-(3,5-diisopropyloxy-4-methoxyphenyl)glycine

(R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Downstream raw materials:

C₄₅H₄₉F₂N₇O₁₆

Refernces

• 1、 Beugelmans, Rene,Bois-Choussy, Michele,Vergne, Caroline,Bouillon, Jean-Philippe,Zhu, Jieping. "Synthesis of a model bicyclic C-O-D-O-E ring of vancomycin by a one-pot, double SNAr based macrocyclization". . p. 1029 - 1030. Retrieved 2007/10/03.