CBZ-D-4-FLUOROPHENYLALANINE

Base Information

• Chemical Name: CBZ-D-4-FLUOROPHENYLALANINE
• CAS No.: 117467-73-9
• Molecular Formula: C17H16 F N O4
• Molecular Weight: 317.317
• Mol file: 117467-73-9.mol

Synonyms:N-Benzyloxycarbonyl-3-(4-fluorophenyl)-D-alanine

Chemical Property of CBZ-D-4-FLUOROPHENYLALANINE

Chemical Property:

• PSA: 75.63000
• LogP: 3.13870
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

Z-D-Phe(4-F)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CBZ-D-4-FLUOROPHENYLALANINE

There total 9 articles about CBZ-D-4-FLUOROPHENYLALANINE 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: 95.0%

ethanol (64-17-5) + DL-Z-4-F-Phe-OH (404-32-0) → L-Z-4-F-Phe-OEt (117402-85-4) + (R)-(N-benzyloxycarbonyl)-p-fluorophenylalanine (117467-73-9)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

Reference yield:

(R)-4-fluorophenylalanine (18125-46-7) + benzyl chloroformate (501-53-1,94274-21-2) → (R)-(N-benzyloxycarbonyl)-p-fluorophenylalanine (117467-73-9)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; for 2h;

Reference yield:

4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester (394210-36-7) → (R)-(N-benzyloxycarbonyl)-p-fluorophenylalanine (117467-73-9) + 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid (17543-58-7)

Guidance literature:

4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester; With methanol; 4 A molecular sieve; In diethyl ether; at -78 ℃; for 31h;

With water; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja011936q

upstream raw materials:

ethanol

DL-Z-4-F-Phe-OH

4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester

4-Fluorophenylalanine

Downstream raw materials:

(4R,5S,6S,7R)-4,7-Bis-(4-fluoro-benzyl)-1,3-bis-(4-hydroxymethyl-benzyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one

(4R,5S,6S,7R)-1,3-Bis-cyclopropylmethyl-4,7-bis-(4-fluoro-benzyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one

(2R,3S,4S,5R)-2.5-bis(N-Cbz-amino)-3,4-dihydroxy-1,6-di(4-fluorophenyl)hexane

[(R)-2-(4-Fluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid benzyl ester

Refernces

• 1、 -. "BORONIC ACID THROMBIN INHIBITORS". Page/Page column 68-69. . Retrieved 2010/02/14.
• 2、 Miyazawa, Toshifumi,Iwanaga, Hitoshi,Ueji, Shinichi,Yamada,Takashi,Kuwata, Shigeru. "Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids". . p. 2219 - 2222. Retrieved 2007/10/02.