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

• 163061-19-6 (2S)-2-tert-butoxycarbonylamino-2-phenylacetaldehyde 
• 100-42-5 styrene 
• 73210-14-7 N-chloro-N-sodio-tert-butylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124718-93-0 2-azido-2-phenylethanol 
• 20989-17-7 (2S)-2-phenylglycinol 
• 56613-80-0 D-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 4248-19-5 tert-butyl carbazate 
• 402741-11-1 (4R,5S)-5-acetoxy-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butylester 
• 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 
• 402741-08-6 (4R,5S)-5-acetyl-3-(4-methoxyphenyl)-4-phenyloxazolidin-2-one 

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 
• 126610-77-3 (R)-tert-butyl N-<1-phenyl-2-<(p-toluenesulfonyl)oxy>ethyl>carbamate 
• 171002-01-0 (S)-N-t-Boc-2-amino-2-phenyl-1-thiophenylethane 
• 180999-32-0 (1-phenyl-2-phenylsulfanyl-ethyl)-carbamic acid tert-butyl ester 
• 177948-29-7 carbamic acid (R)-2-amino-2-phenylethyl ester 
• 928757-29-3 4-bromo-benzoic acid 2-tert-butoxycarbonylamino-2-phenyl-ethyl ester 
• 928757-26-0 2-fluoro-benzoic acid 2-tert-butoxycarbonylamino-2-phenyl-ethyl ester 
• 313352-59-9 C₁₃H₁₈BrNO₂ 
• 454169-97-2 (2'R)-6-bromo-5-[(2'-t-butoxycarbonylamino)-2'-phenylethoxy]-2-isopropoxy-4-(trifluoromethyl)quinoline 
• 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 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.

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.