66605-57-0

Basic information

• Product Name: N-Boc-L-Phenylalaninol
• Synonyms: L-(-)-BOC-PHENYLALANINOL;CARBAMIC ACID, [(1S)-1-(HYDROXYMETHYL)-2-PHENYLETHYL]-, 1,1-DIMETHYLETHYL ESTER;BOC-L-PHENYLALANINOL;BOC-L-PHE-OL;BOC-PHE-OL;BOC-PHENYLALANINOL;BOC-(S)-2-AMINO-3-PHENYL-1-PROPANOL;(S)-(-)-2-(TERT-BUTOXYCARBONYLAMINO)-3-PHENYL-1-PROPANOL
• CAS NO: 66605-57-0
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.32
• EINECS: 1533716-785-6
• Product Categories: chiral;API intermediates;Amino Acids;Phenylalanine [Phe, F];Amino Alcohols;Boc-Amino acid series;Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 66605-57-0.mol
• Article Data: 206

Chemical Properties

• Melting Point: 94-96 °C(lit.)
• Boiling Point: 96-97°C
• Flash Point: 201.8 °C
• Appearance: white to light yellow crystal powder
• Density: 1.0696 (rough estimate)
• Refractive Index: 1.5280 (estimate)
• Storage Temp.: -15°C
• PKA: 12.07±0.46(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 3652004
• CAS DataBase Reference: N-Boc-L-Phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-L-Phenylalaninol(66605-57-0)
• EPA Substance Registry System: N-Boc-L-Phenylalaninol(66605-57-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 66605-57-0(Hazardous Substances Data)

Usage

Description

N-Boc-L-Phenylalaninol, also known as N-(tert-butoxycarbonyl)-L-phenylalaninol, is a white to light yellow crystal powder that serves as a protected form of L-Phenylalaninol. It is a derivative of the naturally occurring amino acid L-Phenylalanine, with an additional tert-butoxycarbonyl (Boc) group attached to the nitrogen atom. This modification enhances the stability of the molecule and prevents unwanted reactions during synthesis processes.

Uses

Used in Pharmaceutical Industry:
N-Boc-L-Phenylalaninol is used as an intermediate in the preparation of (R)-Amphetamine, a compound with significant pharmaceutical applications. The Boc protection allows for the selective synthesis of (R)-Amphetamine without affecting the amino group, ensuring the desired stereochemistry and purity of the final product.
Used in Biochemical Research:
N-Boc-L-Phenylalaninol is employed in the synthesis of biochemically active compounds, which are essential for various research applications. The Boc-protected form of L-Phenylalaninol enables the development of novel compounds with potential therapeutic and diagnostic properties, contributing to the advancement of biochemistry and pharmaceutical sciences.
Used in Chemical Synthesis:
As a protected amino acid derivative, N-Boc-L-Phenylalaninol is used in chemical synthesis to facilitate the formation of complex molecules with specific functional groups. The Boc group can be selectively removed when needed, allowing for further reactions and modifications to be carried out on the L-Phenylalaninol moiety. This versatility makes it a valuable tool in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 335628-25-6 (4S,5R)-4-benzyl-3-tert-butoxycarbonyl-5-methoxy-2-oxazolidinone 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 335627-88-8 (4S,5R)-4-benzyl-5-methoxy-2-oxazolidinone 
• 60-29-7 diethyl ether 
• 75-09-2 dichloromethane 
• 119206-32-5 C₁₉H₂₇NO₆ 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 1025839-59-1 2-tert-butoxycarbonylamino-3-phenyl-propionic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester 
• 251325-58-3 tert-butyl (Z)-(3-hydroxy-1-phenylprop-1-en-2-yl)carbamate 
• 21148-96-9 N-(tert-butoxycarbonyl)-L-phenylalanine pentachlorophenyl ester 
• 149206-46-2 (4S)-4-Benzyl-N-tert-butyloxycarbonyl-1,3-oxazolidin-5-one 
• 207122-29-0 (2S)-2-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-3-phenylpropane 

Downstream Products

• 98900-25-5 2-[2-(tert-butoxycarbonylamino)-3-phenylpropoxy]acetic acid ethyl ester 
• 187526-92-7 [(1S)-1-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-2-phenylethyl]carbamic acid 1,1-dimethylethyl ester 
• 109687-70-9 tert-butyl (S)-(1-phenyl-3-(phenylthio)propan-2-yl)carbamate 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 3182-95-4 L-Phenylalaninol 
• 72155-45-4 Boc-L-phenylalaninal 
• 882170-26-5 [1-(4-bromo-pyridin-3-yloxymethyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 519186-19-7 1-(4-benzyloxyphenoxy)-8-[2-(N-tert-butoxycarbonylamino)-3-phenyl-1-propyloxy]octane 
• 185384-15-0 (S)-tert-butyl (1-bromo-3-phenylpropan-2-yl)carbamate 
• 134557-74-7 tert-butyl [(2S)-1-azido-3-phenylpropan-2-yl]carbamate 
• 178894-52-5 (3R,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-pent-1-yn-3-ol 
• 161828-21-3 (3S,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-pent-1-yn-3-ol 
• 161828-15-5 (3R,4S)-4-[N-(tert-butoxycarbonyl)amino]-1-trimethylsilyl-5-phenyl-pent-1-yn-3-ol 
• 161828-14-4 (3S,4S)-4-[N-(tert-butoxycarbonyl)amino]-1-trimethylsilyl-5-phenyl-pent-1-yn-3-ol 

Relevant articles and documents

Synthesis of Protected Amino Alcohols: A Comparative Study

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Design, Synthesis, and Cytotoxic Activity of New Tubulysin Analogues

Synthesis of tubulysin analogues, containing an N-methyl substituent on tubuvaline-amide together with the replacement of either the hydrophobic N-terminal N-methyl pipecolic acid (Mep) or at both N- and C- terminal peptides with available heteroaromatic

Construction and activity evaluation of novel benzodioxane derivatives as dual-target antifungal inhibitors

Ergosterol exert the important function in maintaining the fluidity and osmotic pressure of fungal cells, and its key biosynthesis enzymes (Squalene epoxidase, SE; 14 α-demethylase, CYP51) displayed the obvious synergistic effects. Therefore, we expected to discover the novel antifungal compounds with dual-target (SE/CYP51) inhibitory activity. In the progress, we screened the different kinds of potent fragments based on the dual-target (CYP51, SE) features, and the method of fragment-based drug discovery (FBDD) was used to guide the construction of three different series of benzodioxane compounds. Subsequently, their chemical structures were synthesized and evaluated. These compounds displayed the obvious biological activity against the pathogenic fungal strains. Notably, target compounds 10a-2 and 22a-2 possessed the excellent broad-spectrum anti-fungal activity (MIC50, 0.125–2.0 μg/mL) and the activity against drug-resistant strains (MIC50, 0.5–2.0 μg/mL). Preliminary mechanism studies have confirmed that these compounds effectively inhibited the dual-target (SE/CYP51) activity, they could cause fungal rupture and death by blocking the bio-synthetic pathway of ergosterol. Further experiments discovered that compounds 10a-2 and 22a-2 also maintained a certain of anti-fungal effect in vivo. In summary, this study not only provided the new dual-target drug design strategy and method, but also discover the potential antifungal compounds.

Design and synthesis of novel phe-phe hydroxyethylene derivatives as potential coronavirus main protease inhibitors

In response to the current pandemic caused by the novel SARS-CoV-2, we design new compounds based on Lopinavir structure as an FDA-approved antiviral agent which is currently under more evaluation in clinical trials for COVID-19 patients. This is the first example of the preparation of Lopinavir isosteres from the main core of Lopinavir conducted to various heterocyclic fragments. It is proposed that main protease inhibitors play an important role in the cycle life of coronavirus. Thus, the protease inhibition effect of synthesized compounds was studied by molecular docking method. All of these 10 molecules, showing a good docking score compared. Molecular dynamics (MD) simulations also confirmed the stability of the best-designed compound in Mpro active site. Communicated by Ramaswamy H. Sarma.