138812-70-1

Basic information

• Product Name: Z-D-HOMOPHE-OH
• Synonyms: CBZ-D-HOMOPHENYL-ALA;CBZ-(R)-2-AMINO-4-PHENYLBUTYRIC ACID;DECALCIFYING SOLUTION A;Z-D-HOMOPHENYLALANINE;Z-D-HOMOPHE-OH;Z-D-HOPHE-OH;Z-D-HPH-OH;(R)-2-(Z-AMINO)-4-PHENYL-BUTYRIC ACID
• CAS NO: 138812-70-1
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.35
• Mol File: 138812-70-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: Store at RT.
• CAS DataBase Reference: Z-D-HOMOPHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-HOMOPHE-OH(138812-70-1)
• EPA Substance Registry System: Z-D-HOMOPHE-OH(138812-70-1)

Safety Data

• Hazardous Substances Data: 138812-70-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Z-D-HOMOPHE-OH is used as a key intermediate in the synthesis of rapamycin-peptide hybrid molecules. These hybrid molecules serve as macrocyclic immunosuppressants, which are crucial in the treatment of autoimmune diseases and prevention of organ transplant rejection. The unique structure of Z-D-HOMOPHE-OH allows for the development of novel immunosuppressants with improved efficacy and reduced side effects.

Upstream product

• 127862-83-3 2-Benzyloxycarbonylamino-4-phenyl-butyric acid 2,2,2-trifluoro-ethyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 82795-51-5 D-homophenylalanine 
• 271260-90-3 benzyl (4R)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate 
• 591-50-4 iodobenzene 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 412917-36-3 benzyl (4R)-2,2-dimethyl-4-(2-phenylethyl)-1,3-oxazolidine-3-carboxylate 
• 142037-77-2 methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoate 
• 501-53-1 benzyl chloroformate 
• 106860-17-7 methyl 2S-2-amino-4-phenylbutanoate 
• 943-73-7 D-homophenylalanine 
• 42940-68-1 phenylacetyl chloride 
• 90891-21-7 L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride 
• 288068-80-4 (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester 

Downstream Products

• 146765-85-7 (S)-2-Benzyloxycarbonylamino-4-phenyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 179901-29-2 [(S)-3-Phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-carbamic acid benzyl ester 
• 615537-52-5 [(S)-1-(3-Oxo-propylcarbamoyl)-3-phenyl-propyl]-carbamic acid benzyl ester 
• 207305-48-4 N-(benzyloxycarbonyl)-homo-L-phenylalaninal 
• 146765-86-8 (R)-2-Benzyloxycarbonylamino-4-phenyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 205493-77-2 (3S,4S)-3-(N-benzyloxycarbonyl-L-homophenylalanyl)-amino-4-acetoxy-azetidin-2-one 
• 162541-33-5 ((S)-1-(S)-Oxiranyl-3-phenyl-propyl)-carbamic acid benzyl ester 
• 165727-47-9 {(1S,2R)-1-Benzyl-3-[((2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-5-phenyl-pentyl)-(2-trimethylsilanyl-ethoxycarbonyl)-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 165727-49-1 ((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-phenyl-pentyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 162538-21-8 [(1S,2R)-3-((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butylamino)-2-hydroxy-1-phenethyl-propyl]-carbamic acid benzyl ester 
• 165727-48-0 {(1S,2R)-3-[((2R,3S)-3-Amino-2-hydroxy-5-phenyl-pentyl)-(2-trimethylsilanyl-ethoxycarbonyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 1026926-41-9 ((S)-3-Chloro-2-oxo-1-phenethyl-propyl)-carbamic acid benzyl ester 
• 1027065-31-1 ((1S,2S)-3-Chloro-2-hydroxy-1-phenethyl-propyl)-carbamic acid benzyl ester 
• 182742-38-7 (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester 

Relevant articles and documents

Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation

Novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation were developed; some of them possess Ki values in the micromolar range. We studied the structure-activity relationship of these derivatives and we performed docking studies, which allowed us to find out the key interactions established by the inhibitors with the target enzyme. Biological results indicate that the nature of the P2 and P3 substituents and their binding to the S2/S3 pockets is strictly interdependent.

COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTlVATING PROTEASE INHIBITORS

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

Compounds and Compositions as Channel Activating Protease Inhibitors

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 2. l-homophenylalanine-based syntheses

Two enantioselective syntheses of the fused benzazepine dopamine D1 antagonist (6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5H-benzo[d]naphth[2,1-b] azepin-12-ol (1) are described in which the starting material is (+)-L-homophenylalan

Poststatin, a new inhibitor of prolyl endopeptidase. V. Endopeptidase inhibitory activity of poststatin analogues

Thirty analogues of poststatin were synthesized, and their inhibitory activities against prolyl endopeptidase, human leukocyte elastase and cathepsin B were measured. The α-ketone was essential and the S configuration was preferable to the R configuration in the β-substituted-β-amino-α-oxopropionic acid moiety of poststatin analogues for endopeptidase inhibitory activity. The analogue in which the D-leucine residue of poststatin was replaced by L-leucine showed strong inhibitory activity to cathepsin B. Introduction of an aromatic group into the P4 position and proline into the P2 position increased inhibitory activity to elastase. Benzyloxycarbonyl-L-homophenylalanyl-(RS)-3-amino-2-oxovaleryl-D- leucyl-L-valine was about 6 times more active to prolyl endopeptidase than natural poststatin.

Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids

Porcine pancreatic lipase catalyzed the highly enantioselective hydrolysis of a kind of α-substituted carboxylic esters, i.e., the 2,2,2-trifluoroethyl esters of the N-benzyloxycarbonyl derivatives of unusual amino acids.