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

Description

Cbz-D-Phenylalaninol, also known as Carbobenzyloxy-D-Phenylalaninol, is a chiral derivative of D-Phenylalaninol with a carbobenzyloxy (Cbz) protecting group. It is a white crystalline solid and is an important intermediate in the synthesis of various pharmaceutical compounds. The Cbz group provides protection to the amino group during chemical reactions, allowing for selective functionalization of other sites on the molecule.

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

• 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 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 1885-14-9 phenyl chloroformate 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 2448-45-5 Cbz-D-Phe 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 62750-39-4 1-<(Benzyl-carbobenzoxyamino)-acetyl>-imidazol 
• 100-46-9 benzylamine 
• 55707-43-2 1-benzyl-2,2-dimethoxyethylamine 
• 59830-61-4 benzyl 1-benzyl-2,2-dimethoxyethylcarbamate 

Downstream Products

• 1101103-75-6 (R)-2-benzyloxycarbonylamino-3-phenylpropyl acetate 
• 1227627-68-0 2-(benzyloxycarbonylamino)-3-phenylpropyl acetate 
• 1053696-57-3 (4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-(4-fluoro-benzyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one 
• 1312443-45-0 (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one 
• 153223-11-1 (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one 
• 170870-15-2 (1R,1'R)-1,1'-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethanamine) 
• 153181-20-5 (2R,3S,4S,5R)-1,6-diphenyl-3,4-bis((2-(trimethylsilyl)ethoxy)methoxy)hexane-2,5-diamine 
• 153181-18-1 dibenzyl ((2R,3S,4S,5R)-1,6-diphenyl-3,4-bis((2-(trimethylsilyl)ethoxy)methoxy)hexane-2,5-diyl)dicarbamate 
• 177574-46-8 dibenzyl ((1R,1'R)-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethane-1,1-diyl))dicarbamate 
• 219586-75-1 (2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol 
• 1053256-39-5 (4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-(4-bromo-benzyl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one 
• 1054613-27-2 (4R,5S,6S,7R)-4,7-Dibenzyl-1-(3-hydroxy-benzyl)-5,6-bis-(2-methoxy-ethoxymethoxy)-3-naphthalen-2-ylmethyl-[1,3]diazepan-2-one 
• 1053696-58-4 (4R,5S,6S,7R)-1-(3-Amino-benzyl)-4,7-dibenzyl-5,6-bis-(2-methoxy-ethoxymethoxy)-3-naphthalen-2-ylmethyl-[1,3]diazepan-2-one 
• 1054682-05-1 (4R,5S,6S,7R)-4,7-Dibenzyl-1-(4-fluoro-benzyl)-5,6-bis-(2-methoxy-ethoxymethoxy)-3-naphthalen-2-ylmethyl-[1,3]diazepan-2-one 

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.

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.