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

• 163061-19-6 (2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 20989-17-7 Phenylglycinol 
• 59410-82-1 (S)-α-phenylglycine ethyl ester hydrochloride 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 591-51-5 phenyllithium 
• 56613-80-0 D-2-phenylglycinol 
• 20989-17-7 (2S)-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 100-42-5 styrene 
• 4248-19-5 tert-butyl carbazate 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 335628-23-4 (4S,5R)-3-tert-butoxycarbonyl-5-methoxy-4-phenyl-2-oxazolidinone 
• 913344-44-2 (-)-di-tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidodicarbonate 

Downstream Products

• 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 
• 171001-99-3 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate 
• 197020-63-6 (S)-tert-butyl 2-phenylaziridine-1-carboxylate 
• 177948-29-7 carbamic acid (R)-2-amino-2-phenylethyl ester 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 479687-18-8 2-oxo-4-phenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 139429-02-0 Thioacetic acid S-((S)-2-tert-butoxycarbonylamino-2-phenyl-ethyl) ester 
• 880360-26-9 (S)-4-Phenyl-5-vinyl-oxazolidin-2-one 
• 880360-35-0 6-phenyl-1-(toluene-4-sulfonyl)-3,6-dihydro-1H-pyridin-2-one 

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 dual-target (SE/CYP51) anti-fungal agents containing amide naphthyl structure

With the increase of fungal infection and drug resistance, it is becoming an urgent task to discover the highly effective antifungal drugs. In the study, we selected the key ergosterol bio-synthetic enzymes (Squalene epoxidase, SE; 14 α-demethylase, CYP51) as dual-target receptors to guide the construction of novel antifungal compounds, which could achieve the purpose of improving drug efficacy and reducing drug-resistance. Three different series of amide naphthyl compounds were generated through the method of skeleton growth, and their corresponding target products were synthesized. Most of compounds displayed the obvious biological activity against different Candida spp. and Aspergillus fumigatus. Among of them, target compounds 14a-2 and 20b-2 not only possessed the excellent broad-spectrum anti-fungal activity (MIC50, 0.125–2 μg/mL), but also maintained the anti-drug-resistant fungal activity (MIC50, 1–4 μg/mL). Preliminary mechanism study revealed the compounds (14a-2, 20b-2) could block the bio-synthetic pathway of ergosterol by inhibiting the dual-target (SE/CYP51) activity, and this finally caused the cleavage and death of fungal cells. In addition, we also discovered that compounds 14a-2 and 20b-2 with low toxic and side effects could exert the excellent therapeutic effect in mice model of fungal infection, which was worthy for further in-depth study.

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.