106454-69-7

Basic information

• Product Name: N-Boc-D-Phenylalaninol
• Synonyms: D-(+)-BOC-PHENYLALANINOL;CARBAMIC ACID, [(1R)-1-(HYDROXYMETHYL)-2-PHENYLETHYL]-, 1,1-DIMETHYLETHYL ESTER;CARBAMIC ACID, [1-(HYDROXYMETHYL)-2,2-DIPHENYLETHYL]-,1,1-DIMETHYLETHYL ESTER, (R)-;BOC-(R)-2-AMINO-3-PHENYL-1-PROPANOL;BOC-D-PHENYLALANINOL;BOC-D-PHE-OL;N-T-BOC-D-PHENYLALANINOL;N-T-BOC-D-PHENYLALANIOL
• CAS NO: 106454-69-7
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.32
• EINECS: 1533716-785-6
• Product Categories: chiral;Amino Acids;Amino Alcohols;Boc-Amino acid series;Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 106454-69-7.mol

Chemical Properties

• Melting Point: 95-98 °C(lit.)
• Boiling Point: 394.48°C (rough estimate)
• Flash Point: 201.8 °C
• Appearance: white to light yellow crystal powder
• Density: 1.0696 (rough estimate)
• Vapor Pressure: 1.84E-07mmHg at 25°C
• Refractive Index: 1.5280 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.07±0.46(Predicted)
• BRN: 4686134
• CAS DataBase Reference: N-Boc-D-Phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-D-Phenylalaninol(106454-69-7)
• EPA Substance Registry System: N-Boc-D-Phenylalaninol(106454-69-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 9-21
• Hazardous Substances Data: 106454-69-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-D-Phenylalaninol is used as an intermediate for the synthesis of (S)-Amphetamine, which is a significant compound in the pharmaceutical industry. Its role in the synthesis process is crucial for the development of various medications with potential therapeutic applications.
Used in Chemical Synthesis:
N-Boc-D-Phenylalaninol is also used as a key component in chemical synthesis, particularly in the production of (S)-Amphetamine. Its unique chemical properties make it a valuable asset in the creation of various compounds with diverse applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C14H21NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h4-8,12,16H,9-10H2,1-3H3,(H,15,17)/t12-/m1/s1

Upstream product

• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 161106-43-0 (R)-4-benzyl-3-t-butoxycarbonyl-2-oxazolidinone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 18942-49-9 Boc-D-Phe-OH 
• 210561-40-3 Hydroxymethyl-((R)-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 219717-95-0 (R)-2-(tert-butoxycarbonylamino)-3-phenylpropyl acetate 
• 251325-58-3 tert-butyl (Z)-(3-hydroxy-1-phenylprop-1-en-2-yl)carbamate 
• 673-06-3 D-(R)-phenylalanine 
• 121056-95-9 trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 
• 100-52-7 benzaldehyde 
• 63658-18-4 methyl (Z)-N-Boc-α,β-didehydrophenylalaninate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 

Downstream Products

• 18942-49-9 Boc-D-Phe-OH 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 126301-19-7 (2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 
• 210561-40-3 Hydroxymethyl-((R)-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 293305-69-8 (R)-2-(N-t-butoxycarbonylamino)-3-phenyl-1-iodopropane 
• 352296-29-8 (R)-5-bromo-3-(N-tert-butoxycarbonyl-2-amino-3-phenylpropyl)-1-(2,6-difluorobenzyl)-6-methyluracil 
• 951035-64-6 (R,Z)-tert-butyl 1-phenylhex-3-en-2-ylcarbamate 
• 951035-65-7 2-hydroxy-N-((S)-1-phenylhexan-2-yl)pentadecanamide 
• 87982-85-2 (S)-(+)-1-Phenylhexan-2-ylamine 
• 260998-65-0 (S)-(-)-N-(tert-Butoxycarbonyl)-1-phenylhexan-2-ylamine 
• 283589-06-0 (R)-1-Bromomethyl-2-phenyl-ethylamine; hydrobromide 
• 482374-27-6 (1-benzyl-2-hydroxy-3-methyl-but-3-enyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents

A rate enhancement of tert-butoxycarbonylation of aromatic amines by Boc2O in alcohols compared to aprotic solvents was demonstrated. Kinetic analysis by NMR suggested that the reaction in CD3OD was faster than in CDCl3 by a factor of 70. Reactions between Boc2O and various aliphatic and aromatic amines in ethanol provided the N-Boc derivatives in good to excellent yields in short reaction times.

Synthesis and biological activity of cyclolinopeptide A analogues modified with γ4-bis(homo-phenylalanine)

Cyclolinopeptide A (CLA), an immunosuppressive nonapeptide derived from linen seeds, was modified with S or R-γ4-bis(homo-phenylalanine) in positions 3 or 4, or both 3 and 4. These modifications changed the flexibility of new analogues and distribution of intramolecular hydrogen bonds. Analogues 11 c(Pro1-Pro2-Phe3-S-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9), 13 c(Pro1-Pro2-S-γ4-hhPhe3-R-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9) and 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) existed as a mixture of stable cis/trans isomers of Pro-Pro peptide bond. The comparison of the relative spatial orientations in crystal state of the two carbonyl groups, neighboring γ-amino acids, revealed conformational similarities to α-peptides. The addition of two -CH2- groups in γ-amino acids led to a more rigid conformation, although a more flexible one was expected. A significant difference in the relative orientation of the carbonyl groups was found for cyclic γ-peptides with a dominance of an antiparallel arrangement. As carbonyl groups may be engaged in the interactions with plausible receptors through hydrogen bonds, a similar biological activity of the modified peptides was expected. Our biological studies showed that certain cyclic, but not the corresponding linear peptides, lowered the viability of peripheral blood mononuclear cells (PBMC) at 100?μg/mL concentration. The proliferation of PBMC induced by phytohemagglutinin A (PHA) was strongly inhibited by cyclic peptides only, in a dose-dependant manner. On the other hand, lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-α) production in whole blood cell cultures was inhibited by both linear and cyclic peptides. Peptide 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) blocked the expression of caspase-3, inhibited the expression of caspases-8 and -9 in 24?h culture of Jurkat cells, and caused DNA fragmentation in these cells, as an indicator of apoptosis. Thus, we revealed a new mechanism of immunosuppressive action of a nonapeptide.

Facile synthesis of D-amino acids from an L-serine-derived aziridine

Using the concept that L-serine can be converted into a desymmetrized γ-diol derivative, five D-amino acids were synthesized from a common aziridine intermediate by a general, high-yielding three-step process. The key 2-t-butyldimethylsiloxymethyl N-t-butoxycarbonyl aziridine intermediate was synthesized in four steps and 65% overall yield.

A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions

A green and simple approach for the N-Boc protection on structurally diverse amines under ultrasound irradiation is described. Selective N-Boc protection was achieved in excellent isolated yield in a short reaction time at room temperature. Mild conditions, inexpensive and an easily available reagent, and absence of any auxiliary substances are the main advantages of this procedure. Graphical abstract: [Figure not available: see fulltext.]

Stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid

A highly stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid was achieved by simple addition of diethyl phosphite to enantiomeric N-blocked phenylalaninals. These compounds exhibit significant herbicidal activity.

Highly enantioselective hydrogenation of α-oxy functionalized α,β-unsaturated acids catalyzed by a ChenPhos-Rh complex in CF3CH2OH

Rhodium complexes coordinated by Chenphos are very effective catalysts for the enantioselective hydrogenation of α-aryloxy- and α-alkoxy-substituted α,β-unsaturated carboxylic acids under mild conditions in CF3CH2OH. The catalytic system could be successfully employed in building the core structure of a new FDA approved drug LCZ 696.

PROCESS FOR PREPARATION OF SOLRIAMFETOL AND INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of dopamine and norepinephrine reuptake inhibitor (DNRI) compound Solriamfetol and pharmaceutically acceptable salts thereof, having the chemical name (R)-2-amino- 3-phenylpropyl carbamate (APC) by using novel intermediates. (I)

Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution

Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine. These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (~380 nm) with a relatively large Stokes shift (5700 cm?1). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40–80%) of compared to the sulfur analogues (3–6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to π-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions.

PEPTIDE-OLIGOUREA HYBRID COMPOUNDS

The present description relates to peptidomimetic foldamers, and their synthesis. In particular, the description provides peptide-amino urea hybrid peptidomimetic foldamers comprising an alpha amino acid peptide portion and an oligourea portion.

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production

The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.