58917-85-4

Basic information

• Product Name: Cbz-D-Phenylalaninol
• Synonyms: (R)-(+)-2-(Carbobenzyloxyamino)-3-phenyl-1-propanol,99%;(R)-(+)-2-(Cbz-aMino)-3-phenyl-1-propanol;(R)-N-Carbobenzoxy-2-amino-3-phenyl-1-propanol (R)-N-Cbz-2-amino-3-phenyl-1-propanol N-Cbz-D-phenylalaninol;Cbz-D-Phenylalanino;(R)-benzyl 1-hydroxy-3-phenylpropan-2-ylcarbamate;Cbz-D-Phe-OL;Z-D-phenylalaninol≥ 99% (HPLC);N-CARBOBENZOXY-D-PHENYLALANINOL
• CAS NO: 58917-85-4
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34
• EINECS: 1533716-785-6
• Product Categories: Pyridines ,Heterocyclic Acids;chiral;Amino Alcohols;Z-Amino acid series
• Mol File: 58917-85-4.mol

Chemical Properties

• Melting Point: 92-95 °C
• Boiling Point: 427.77°C (rough estimate)
• Flash Point: 249.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.0864 (rough estimate)
• Vapor Pressure: 2.23E-10mmHg at 25°C
• Refractive Index: 42 ° (C=2, MeOH)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 11.86±0.46(Predicted)
• BRN: 2221968
• CAS DataBase Reference: Cbz-D-Phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-D-Phenylalaninol(58917-85-4)
• EPA Substance Registry System: Cbz-D-Phenylalaninol(58917-85-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 58917-85-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Cbz-D-Phenylalaninol is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications. Its chiral nature and the presence of the Cbz protecting group make it a versatile building block for the development of enantioselective synthetic routes.
Used in the Synthesis of Aminophosphines:
Cbz-D-Phenylalaninol is used as a precursor in the synthesis of aminophenylpropanyl phosphate derivatives, which exhibit pin1 inhibitory activity. Pin1 is a peptidyl-prolyl isomerase enzyme that plays a crucial role in various cellular processes, and its inhibition has been implicated in the treatment of various diseases, including cancer and neurodegenerative disorders.
Used in Drug Delivery Systems:
Cbz-D-Phenylalaninol can be incorporated into drug delivery systems to improve the bioavailability and therapeutic efficacy of the synthesized pharmaceutical compounds. The Cbz protecting group can be selectively removed under mild conditions, allowing for the controlled release of the active pharmaceutical ingredient.

InChI:InChI=1/C17H19NO3/c19-12-16(11-14-7-3-1-4-8-14)18-17(20)21-13-15-9-5-2-6-10-15/h1-10,16,19H,11-13H2,(H,18,20)/t16-/m1/s1

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 
• 300-57-2 allylbenzene 
• 1262306-22-8 benzyloxycarbonylamino-4-chlorobenzoate 
• 501-53-1 benzyl chloroformate 
• 1217341-14-4 C₁₈H₂₃NO₂ 
• 1084820-37-0 1,1-dimethoxy-3-phenylpropan-2-one oxime 
• 59830-60-3 N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde 
• 59830-61-4 benzyl 1-benzyl-2,2-dimethoxyethylcarbamate 
• 55707-43-2 1-benzyl-2,2-dimethoxyethylamine 
• 100-46-9 benzylamine 
• 3588-57-6 Z-DL-Phe-OH 
• 62750-39-4 1-<(Benzyl-carbobenzoxyamino)-acetyl>-imidazol 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 

Downstream Products

• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 59830-60-3 N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde 
• 502616-48-0 [(R)-1-Benzyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-carbamic acid benzyl ester 
• 611210-20-9 (1R)-1-(1,3-dioxolan-2-yl)-2-phenylethanamine 
• 611210-33-4 (2S)-N-[(1R)-1-(1,3-dioxolan-2-yl)-2-phenylethyl]-2-hydroxy-4-methylpentanamide 
• 502616-45-7 1-benzyl-2-[2-(trimethylsilyl)ethoxymethoxy]ethylamine 
• 58970-76-6 bestatin 
• 301544-46-7 (S)-2-((R)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester 
• 249296-51-3 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-ol 
• 105507-42-4 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-one 
• 153223-11-1 (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one 
• 151867-81-1 DMP 323 

Relevant articles and documents

A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H

N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.

Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes

The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Resolution of N-Protected amino alcohols by porcine pancreatic lipase

The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.

Carbamate derivatives of felbamate as potential anticonvulsant agents

Several monocarbamate compounds derived from felbamate were synthesized and 11 target compounds (1, 4, and 6-14) were initially evaluated in mice MES and PTZ models in our laboratory. Carbamate compounds with varying substituents on the oxygen (1-4) gave anticonvulsant activity with a wide range of ED 50 in MES test from 300 mg/kg (4) and compounds with different groups on the nitrogen (5-14) also were quite active in the range of 15 mg/kg (14) to 170.5 mg/kg (6). This suggested that the spatial limitation in the MES model seemed flexible especially on the nitrogen end. All tested compounds showed some activity against mice scPTZ test, but none had the ED50 value 50 mg/kg. Ten selected compounds (1 and 6-14) for subsequent pharmacological evaluation in NIH all gave positive mice MES activity except 8 and 9, which were unexpectedly active in rats after further evaluations. Among the compounds, 1, 8, and 9 advanced to the quantitative study and 1 and 9 provided the highest PI values, 15 and 21, respectively, in the rat oral MES test.

Structure-based design of novel human Pin1 inhibitors (I)

Pin1 is a member of the cis-trans peptidyl-prolyl isomerase family with potential anti-cancer therapeutic value. Here we report structure-based de novo design and optimization of novel Pin1 inhibitors. Without a viable lead from internal screenings, we de

Phosphate/sulfate ester compounds and pharmaceutical composition for inhibiting protein interacting NIMA (PIN1)

Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.

NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS

The present invention is directed to compositions comprising lysophosphatidic acid analogs and methods of using such analogs as agonist or antagonists of LPA receptor activity. In addition the invention is directed to LPA receptor agonists that vary in the degree of selectivity at individual LPA receptors (i.e. LPA1, LPA2 and LPA3). More particularly the present invention is directed to LPA analogs wherein the glycerol is replaced with ethanolamine and a variety of substitutions have been linked at the second carbon atom.

PHOSPHATE/SULFATE ESTER COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING PROTEIN INTERACTING NIMA (PIN1)

Phosphate/sulfate ester compounds that modulate and/or inhibit the activity of protein interacting NIMA (PIN1), and to pharmaceutical compositions containing such compounds are described. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating disorders characterized by hypertension, inappropriate cell proliferation, infectious diseases, and neurodegenerative brain disorders, by administering effective amounts of such compounds.