117049-14-6

Basic information

• Product Name: BOC-L-Phenylglycinol
• Synonyms: CARBAMIC ACID, [(1S)-2-HYDROXY-1-PHENYLETHYL]-, 1,1-DIMETHYLETHYL ESTER;BOC-L-PHENYLGLYCINOL;BOC-PHG-OL;BOC-PHENYLGLYCINOL;TBOC-L-PHENYLGLYCINOL;(S)-N-BOC-2-PHENYLGLYCINOL;(S)-(+)-N-(TERT-BUTOXYCARBONYL)-2-PHENYLGLYCINOL;(S)-N-(TERT-BUTOXYCARBONYL)-2-PHENYLGLYCINOL
• CAS NO: 117049-14-6
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29
• EINECS: -0
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 117049-14-6.mol
• Article Data: 132

Chemical Properties

• Melting Point: 136-139 °C(lit.)
• Boiling Point: 382.4 °C at 760 mmHg
• Flash Point: 185 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.55±0.46(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 4316842
• CAS DataBase Reference: BOC-L-Phenylglycinol(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-Phenylglycinol(117049-14-6)
• EPA Substance Registry System: BOC-L-Phenylglycinol(117049-14-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 117049-14-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

N-Boc-L-alpha-phenylglycinol is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dye fields. Phenylglycinol-derived oxazolopiperidone lactams is used as starting materials for the enantioselective synthesis of piperidine-containing alkaloids.

InChI:InChI=1/C13H19NO3/c1-13(2,3)17-12(16)14-9-11(15)10-7-5-4-6-8-10/h4-8,11,15H,9H2,1-3H3,(H,14,16)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 20989-17-7 (2S)-2-phenylglycinol 
• 163061-19-6 (2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde 
• 143978-88-5 N-tert-butoxycarbonyl-L-phenylglycine methyl ester 
• 100-42-5 styrene 
• 4248-19-5 tert-butyl carbazate 
• 335628-23-4 (4S,5R)-3-tert-butoxycarbonyl-5-methoxy-4-phenyl-2-oxazolidinone 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 402741-11-1 (4R,5S)-5-acetoxy-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butylester 
• 126610-76-2 Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 56613-80-0 D-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 100-52-7 benzaldehyde 
• 402741-05-3 (1R,2S)-2-hydroxy-1-(4-methoxyphenylamino)-1-phenylbutan-3-one 

Downstream Products

• 171001-99-3 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate 
• 177948-29-7 carbamic acid (R)-2-amino-2-phenylethyl ester 
• 476352-85-9 [2-(isoquinolin-7-yloxy)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 606144-71-2 tert-butyl (1R)-2-{[(1R,2S)-3-cyano-1-methyl-2-(phenylseleno)propyl]oxy}-1-phenylethylcarbamate 
• 606144-70-1 tert-butyl (1R)-2-{[(1S,2R)-3-cyano-1-methyl-2-(phenylseleno)propyl]oxy}-1-phenylethylcarbamate 
• 606144-82-5 methyl (3RS,4SR)-4-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl}oxy)-3-(phenylseleno)pentanoate 
• 606144-84-7 methyl (3S,4R)-4-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl}oxy)-4-phenyl-3-(phenylseleno)butanoate 
• 606144-83-6 methyl (3R,4S)-4-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl}oxy)-4-phenyl-3-(phenylseleno)butanoate 
• 691871-79-1 [(1S,2S)-2-Hydroxy-1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid tert-butyl ester 
• 647035-71-0 (+)-N-nosyl-N-((R)-2-(tert-butyloxycarbonylamino)-2-phenylethyl)benzenamine 
• 928757-28-2 3-bromo-benzoic acid 2-tert-butoxycarbonylamino-2-phenyl-ethyl ester 
• 352290-59-6 3-(2-amino-2-phenyl-ethyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 562817-60-1 (2S,3S)-1-(tert-butyloxycarbonyl)-2-phenyl-3-[(3,5)-bis(trifluoromethyl)benzyloxy]piperidine 
• 599156-27-1 allyl-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-but-3-enyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)3Cl2·6H2O and benzoylperoxide (BzO)2. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

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.

Visible-Light-Induced Intermolecular Oxyimination of Alkenes

An intermolecular vicinal O-N difunctionalization reaction of olefins with oxime esters through energy transfer catalysis has been developed.