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
• Article Data: 17

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

Chemical Properties

white to light yellow crystal powde

Uses

Z-D-Phenylalaninol is used in the synthesis of aminophenylpropanyl phosphate derivatives which has pin1 inhibitory activity.

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 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 1885-14-9 phenyl chloroformate 
• 1235475-84-9 C₁₉H₂₁NO₄ 
• 3588-57-6 Z-DL-Phe-OH 
• 121335-13-5 2-Benzyloxycarbonylamino-3-phenyl-propionic acid 6-nitro-benzotriazol-1-yl ester 
• 2448-45-5 Cbz-D-Phe 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 62750-39-4 1-<(Benzyl-carbobenzoxyamino)-acetyl>-imidazol 

Downstream Products

• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 59830-60-3 N-benzyloxycarbonyl-2-amino-3-phenylpropionaldehyde 
• 249296-51-3 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-ol 
• 105507-42-4 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-one 
• 1101103-75-6 (R)-2-benzyloxycarbonylamino-3-phenylpropyl acetate 
• 1227627-68-0 2-(benzyloxycarbonylamino)-3-phenylpropyl acetate 
• 1235475-84-9 C₁₉H₂₁NO₄ 
• 301544-46-7 (S)-2-((R)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester 
• 58970-76-6 bestatin 
• 502616-45-7 1-benzyl-2-[2-(trimethylsilyl)ethoxymethoxy]ethylamine 
• 611210-33-4 (2S)-N-[(1R)-1-(1,3-dioxolan-2-yl)-2-phenylethyl]-2-hydroxy-4-methylpentanamide 

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.

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.

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.