869468-32-6

Basic information

• Product Name: N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester
• Synonyms: N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester;Cbz-S-3-aMino-3-phenylpropan-1-ol;(S)-Cbz-3-AMino-3-phenylpropan-1-ol;[(1R)-3-Hydroxy-1-phenylpropyl]carbaMic acid phenylMethyl ester;Benzyl [(1S)-3-hydroxy-1-phenylpropyl]carbaMate;N-[(1S)-3-hydroxy-1-phenylpropyl]Carbamic acid phenylmethyl ester
• CAS NO: 869468-32-6
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285
• Mol File: 869468-32-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 483.316 °C at 760 mmHg
• Flash Point: 246.101 °C
• Appearance: /
• Density: 1.174
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.56±0.46(Predicted)
• CAS DataBase Reference: N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester(869468-32-6)
• EPA Substance Registry System: N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester(869468-32-6)

Safety Data

• Hazardous Substances Data: 869468-32-6(Hazardous Substances Data)

Usage

General Description

N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester, also known as N-protected phenylalanine, is a chemical compound commonly used in peptide synthesis. It is an ester derivative of carbamic acid and contains a benzyl group. N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester is important in the production of pharmaceuticals and is used as a building block in the synthesis of various peptides. It is a white crystalline solid with a molecular formula of C17H17NO3 and a molecular weight of 287.32 g/mol. N-[(1S)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester is a valuable chemical in organic synthesis and plays a crucial role in the development of therapeutic drugs and medications.

Upstream product

• 869468-28-0 (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-phenylpropanamide 
• 31139-36-3 dibenzyl dicarbonate 
• 102-92-1 Cinnamoyl chloride 
• 678991-36-1 E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-phenylprop-2-enamide 
• 678991-41-8 (+)-(1'S,2'S,3S)-3-dibenzylamino-N-methyl-3-phenyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)propanamide 
• 1202160-37-9 3-Cbz-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 32975-59-0 methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate 
• 14441-08-8 (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid 
• 37088-68-9 methyl (S)-3-amino-3-phenylpropanoate tartaric salt 
• 100-52-7 benzaldehyde 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 

Downstream Products

• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 376348-65-1 4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide 

Relevant articles and documents

Structure-Based Design and Development of Chemical Probes Targeting Putative MOR-CCR5 Heterodimers to Inhibit Opioid Exacerbated HIV-1 Infectivity

Crystal structures of ligand-bound G-protein-coupled receptors provide tangible templates for rationally designing molecular probes. Herein, we report the structure-based design, chemical synthesis, and biological investigations of bivalent ligands targeting putative mu opioid receptor C-C motif chemokine ligand 5 (MOR-CCR5) heterodimers. The bivalent ligand VZMC013 possessed nanomolar level binding affinities for both the MOR and CCR5, inhibited CCL5-stimulated calcium mobilization, and remarkably improved anti-HIV-1BaL activity over previously reported bivalent ligands. VZMC013 inhibited viral infection in TZM-bl cells coexpressing CCR5 and MOR to a greater degree than cells expressing CCR5 alone. Furthermore, VZMC013 blocked human immunodeficiency virus (HIV)-1 entry in peripheral blood mononuclear cells (PBMC) cells in a concentration-dependent manner and inhibited opioid-accelerated HIV-1 entry more effectively in phytohemagglutinin-stimulated PBMC cells than in the absence of opioids. A three-dimensional molecular model of VZMC013 binding to the MOR-CCR5 heterodimer complex is constructed to elucidate its mechanism of action. VZMC013 is a potent chemical probe targeting MOR-CCR5 heterodimers and may serve as a pharmacological agent to inhibit opioid-exacerbated HIV-1 entry.

Asymmetric synthesis of maraviroc (UK-427,857)

The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.

Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A bulk enabling synthesis of the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1), is presented. Synthesis of the three key fragments, β-amino ester 3,4,4-difluorohexanecarboxylic acid (2), and 1,3,4-triazole-substituted tropane fragment 4 are described. Coupling strategies for these fragments are discussed and described, including synthetic challenges, protection strategies, impurity generation, and final scale-up of the developed route to 1.