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

Description

BOC-L-Phenylglycinol, also known as N-Boc-L-alpha-phenylglycinol, is a white solid that serves as a crucial intermediate in various chemical syntheses. It is widely recognized for its role in the production of pharmaceuticals, agrochemicals, and dyes, as well as being a key component in the enantioselective synthesis of piperidine-containing alkaloids.

Uses

Used in Organic Synthesis:
BOC-L-Phenylglycinol is used as a vital intermediate for organic synthesis, facilitating the creation of a diverse range of chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BOC-L-Phenylglycinol is utilized as an essential raw material for the development of various medications, contributing to the advancement of healthcare solutions.
Used in Agrochemical Applications:
BOC-L-Phenylglycinol is employed as a key component in the production of agrochemicals, playing a significant role in the development of pesticides and other agricultural products to enhance crop protection and yield.
Used in Dye Industry:
Within the dye industry, BOC-L-Phenylglycinol serves as a critical raw material for the synthesis of various dyes, enabling the creation of a wide array of colors and pigments for different applications.
Used in Enantioselective Synthesis:
BOC-L-Phenylglycinol is used as a starting material for the enantioselective synthesis of piperidine-containing alkaloids, a process that is vital for the production of specific pharmaceutical compounds with desired chiral properties.

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 
• 2935-35-5 (S)-2-phenylglycine 
• 6591-61-3 (S)-Phenylglycine methyl ester 
• 100-52-7 benzaldehyde 
• 402741-05-3 (1R,2S)-2-hydroxy-1-(4-methoxyphenylamino)-1-phenylbutan-3-one 
• 402741-09-7 (4R,5S)-5-acetyl-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 140372-83-4 (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 
• 141096-36-8 (R)-1-Phenyl-2-phenylselanyl-ethylamine 
• 141096-35-7 (R)-2-(diphenylphosphanyl)-1-phenylethan-1-amine 
• 163061-19-6 (2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde 
• 138457-47-3 1-azido-2-phenyl-2-(N-tert-butoxycarbonylamino)ethane 
• 2900-27-8 2-(tert-butoxycarbonylamino)-2-phenylacetic acid 
• 33125-05-2 Boc-D-Phg-OH 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 137284-11-8 (2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 110143-62-9 (S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester 
• 102089-75-8 (-)-(1R)-1-[(1',1'-dimethylethoxycarbonyl)amino]-2-(methylsulfonyl)oxy-1-phenylethane 
• 126610-77-3 (R)-tert-butyl N-<1-phenyl-2-<(p-toluenesulfonyl)oxy>ethyl>carbamate 
• 139429-02-0 Thioacetic acid S-((S)-2-tert-butoxycarbonylamino-2-phenyl-ethyl) 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.

Organoiodine-Catalyzed Enantioselective Intermolecular Oxyamination of Alkenes

Metal-free, catalytic enantioselective intermolecular oxyamination of alkenes is realized by use of organoiodine(I/III) chemistry. The protocol is applicable toward aryl- and alkyl-substituted alkenes with high enantioselectivity and electronically controlled regioselectivity. The oxyaminated products can be easily deprotected in one step to reveal free amino alcohols in high yields without loss of enantioselectivity. A key to our success is the discovery of a virtually unexplored chemical entity, N-(fluorosulfonyl)carbamate, as a bifunctional N,O-nucleophile.