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

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 66605-57-0 differently. You can refer to the following data:
1. Protected L-Phenylalaninol, an intermediate in the preparation of (R)-Amphetamine.
2. N-Boc-L-phenylalaninol is employed in the synthesis of biochemically active compounds.

Upstream product

• 4522-04-7 ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninate 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 149206-46-2 (4S)-4-Benzyl-N-tert-butyloxycarbonyl-1,3-oxazolidin-5-one 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 60-29-7 diethyl ether 
• 75-09-2 dichloromethane 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 83351-75-1 tert-butyl (S)-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 

Downstream Products

• 185384-15-0 (S)-tert-butyl (1-bromo-3-phenylpropan-2-yl)carbamate 
• 129778-81-0 (1S,2S)-(tert-butoxy)-N-[2-hydroxy-1-benzylpent-4-enyl]carboxamide 
• 109687-70-9 tert-butyl (S)-(1-phenyl-3-(phenylthio)propan-2-yl)carbamate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 592507-39-6 (2-cyclohexa-1,4-dienyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 519186-19-7 1-(4-benzyloxyphenoxy)-8-[2-(N-tert-butoxycarbonylamino)-3-phenyl-1-propyloxy]octane 
• 134557-74-7 tert-butyl [(2S)-1-azido-3-phenylpropan-2-yl]carbamate 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 141403-49-8 (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-phenyl-O-(4-methylphenylsulfonyl)propan-1-ol 
• 98900-25-5 2-[2-(tert-butoxycarbonylamino)-3-phenylpropoxy]acetic acid ethyl ester 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 154669-56-4 (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-iodo-3-phenylpropane 

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.

Urea based foldamers

N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.