153223-10-0

Basic information

• Product Name: (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol
• Synonyms: (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol
• CAS NO: 153223-10-0
• Molecular Weight: 568.67
• Mol File: 153223-10-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol(153223-10-0)
• EPA Substance Registry System: (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol(153223-10-0)

Safety Data

• Hazardous Substances Data: 153223-10-0(Hazardous Substances Data)

Upstream product

• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 
• 120452-49-5 N-methoxy-N-methyl-(R)-N²-Cbz-phenylalaninamide 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 2448-45-5 Cbz-D-Phe 

Downstream Products

• 1053712-24-5 ((1R,2S,3S,4R)-1-Benzyl-4-benzyloxycarbonylamino-5-phenyl-2,3-bis-triethylsilanyloxy-pentyl)-carbamic acid benzyl ester 
• 153181-18-1 dibenzyl ((2R,3S,4S,5R)-1,6-diphenyl-3,4-bis((2-(trimethylsilyl)ethoxy)methoxy)hexane-2,5-diyl)dicarbamate 
• 1004316-75-9 C₃₅H₃₄N₂O₆S 
• 151867-81-1 DMP 323 
• 153223-21-3 XK₂₃₄ 
• 153223-23-5 XL₀₇₅ 
• 153181-22-7 (4R,5S,6S,7R)-hexahydro-5,6-bis[2-(trimethylsilyl)ethoxymethoxy]-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one 
• 206853-76-1 (4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-cyclopropylmethyl-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one 
• 1053642-16-2 (4R,5S,6S,7R)-1,3,4,7-Tetrabenzyl-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one 
• 153223-11-1 (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one 
• 170028-72-5 (3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-e][1,3]diazepin-6(7H)-one 
• 1312443-45-0 (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one 
• 219586-75-1 (2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol 
• 153181-58-9 (4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-(4-benzyloxy-benzyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-ylidene-cyanamide 

Relevant articles and documents

Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

A novel and efficient synthesis of chiral C2-symmetric 1,4-diamines

A novel and efficient method for synthesis of (R,R)- and (S,S)-C2-symmetric 1,4-diamines was established. The key steps are a combination of Pinacol Coupling and Corey-Winter olefination.

Stereoisomers of cyclic urea HIV-1 protease inhibitors: Synthesis and binding affinities

We have synthesized stereoisomers of cyclic urea HIV-1 protease inhibitors to study the effect of varying configurations on binding affinities. Four different synthetic approaches were used to prepare the desired cyclic urea stereoisomers. The original cy

Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led te intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed te prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.

Preparation and structure-activity relationship of novel P1/P1'- substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors

A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.