35909-92-3

Basic information

• Product Name: Z-PHE-OME
• Synonyms: CBZ-L-PHENYLALANINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-PHENYLALANINE METHYL ESTER;Z-PHENYLALANINE-OME;Z-PHE-OME;Z-L-PHENYLALANINE METHYL ESTER;N-benzyloxycarbonylphenylalanine methyl ester;N-Benzyloxycarbonylphenyl-L-alanine methyl ester;(2S)-2-[(Benzyloxycarbonyl)amino]-3-phenylpropanoic acid methyl ester
• CAS NO: 35909-92-3
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.35
• Mol File: 35909-92-3.mol
• Article Data: 73

Chemical Properties

• Boiling Point: 478.5°Cat760mmHg
• Flash Point: 243.2°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-PHE-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHE-OME(35909-92-3)
• EPA Substance Registry System: Z-PHE-OME(35909-92-3)

Safety Data

• Hazardous Substances Data: 35909-92-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish oil

InChI:InChI=1/C18H19NO4/c1-22-17(20)16(12-14-8-4-2-5-9-14)19-18(21)23-13-15-10-6-3-7-11-15/h2-11,16H,12-13H2,1H3,(H,19,21)

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 128369-71-1 (S)-methyl-(N-allyloxycarbonyl)phenylalaninate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 16881-34-8 N-benzyloxycarbonyl-L-phenylalanine t-butyl ester 
• 94026-30-9 di(chlorobenzyl) carbonate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 173300-84-0 1,3-Bis(benzyloxycarbonyl)-3,4,5,6-tetrahydropyrimidine-2-thione 
• 186581-53-3 diazomethane 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 4525-33-1 dimethyl dicarbonate 

Downstream Products

• 111610-51-6 (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-propionic acid sec-butyl ester 
• 118209-03-3 Z-Phe-Gly-D-Ala-OMe 
• 118209-05-5 Z-Phe-Gly-D-Phe-OMe 
• 28944-94-7 Z-L-Phe-D-Ala-OMe 
• 102579-45-3 Z-Phe-glycinal dimethyl acetal 
• 1161-13-3 N-Cbz-L-Phe 
• 17187-05-2 Z-L-phenylalanylglycinamide 
• 69193-11-9 Z-L-Phe-L-Val-NH₂ 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 3618-96-0 (S)-N-acetylphenylalanine 
• 129397-81-5 methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate 
• 347851-53-0 dimethyl [(3S)-4-phenyl-3-[(benzyloxycarbonyl)amino]-2-oxobutyl]phosphonate 
• 143601-45-0 (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-5-phenylpentanoate 
• 3588-57-6 Z-DL-Phe-OH 

Relevant articles and documents

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During the BOP-mediated esterification of carboxylic acids, the benzotriazolyl "esters" are formed and then transesterified by the alcohol. The experimental conditions are not critical.

Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome

A series of tripeptidic proteasome inhibitors with furylketone as C-terminus were designed and synthesized. Biochemical evaluations against β1, β2 and β5 subunits revealed that they acted selectively on β5 subunit with IC50s against chymotrypsin-like (CT-L) activity in micromolar range. LC-MS/MS analysis of the ligand-20S proteasome mixture showed that the most potent compound 11m (IC50 = 0.18 μM) made no covalent modification on 20S proteasome. However, it was identified acting in a slowly reversible manner in wash-out assay and the reversibility was much lower than that of MG132, suggesting the possibility of these tripeptidic furylketones forming reversible covalent bonds with 20S proteasome. Several compounds were selected for anti-proliferative assay towards multiple cancer cell lines, and compound 11m displayed comparable potency to positive control (MG132) in all cell lines tested. Furthermore, the pharmacokinetic (PK) data in rats indicated 11m behaved similarly (Cmax, 2007 μg/L; AUC0?t, 680 μg/L·h; Vss, 0.66 L/kg) to the clinical used agent carfilzomib. All these data suggest 11m is a good lead compound to be developed to novel anti-tumor agent.

BABIPhos Family of Biaryl Dihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation

Novel bidentate phosphine ligands BABIPhos featuring a biaryl bis-dihydrobenzooxaphosphole core are presented. Their synthesis was achieved via Pd-catalyzed reductive homocoupling of dihydrobenzooxaphosphole aryl triflates. An efficient route toward various analogues was also established, giving access to phosphines with different electronic and steric properties. The newly obtained ligands demonstrated high efficiency and selectivity in Rh-catalyzed asymmetric hydrogenation of di- and trisubstituted enamides. This new class of ligands is complementary to previously described bidentate benzooxaphosphole ligands BIBOP.