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

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

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 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 869111-27-3 phenethyl tosyloxycarbamate 
• 20989-17-7 Phenylglycinol 
• 169512-94-1 (+/-)-N-tert-butoxycarbonyl-α-phenylglycine methyl ester 
• 2900-27-8 2-(tert-butoxycarbonylamino)-2-phenylacetic acid 
• 875-74-1 (R)-phenylglycine 
• 126923-26-0 (R)-2-azido-2-phenylethan-1-ol 
• 402741-11-1 (4R,5S)-5-acetoxy-2-oxo-4-phenyloxazolidine-3-carboxylic acid tert-butylester 
• 100-42-5 styrene 
• 4248-19-5 tert-butyl carbazate 
• 56613-80-0 D-2-phenylglycinol 
• 6591-61-3 (S)-Phenylglycine methyl ester 

Downstream Products

• 552331-46-1 (2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 313352-59-9 C₁₃H₁₈BrNO₂ 
• 1147272-54-5 C₂₃H₂₆ClN₇O₄ 
• 1197006-13-5 C₁₅H₂₃NO₃ 
• 1197006-14-6 C₁₉H₂₃NO₃ 
• 1242073-15-9 [(1S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-phenylethyl]carbamic acid 1,1-dimethylethyl ester 
• 143394-39-2 (S)-(+)-2-(N-methylamino)-2-phenylethanol 
• 104700-39-2 (E)-ethyl 4-(tert-butoxycarbonylamino)-4-phenylbut-2-enoate 

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.

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.

Identification of Clinical Candidate M2698, a Dual p70S6K and Akt Inhibitor, for Treatment of PAM Pathway-Altered Cancers

Herein, we report the discovery of a novel class of quinazoline carboxamides as dual p70S6k/Akt inhibitors for the treatment of tumors driven by alterations to the PI3K/Akt/mTOR (PAM) pathway. Through the screening of in-house proprietary kinase library, 4-benzylamino-quinazoline-8-carboxylic acid amide 1 stood out, with sub-micromolar p70S6k biochemical activity, as the starting point for a structurally enabled p70S6K/Akt dual inhibitor program that led to the discovery of M2698, a dual p70S6k/Akt inhibitor. M2698 is kinase selective, possesses favorable physical, chemical, and DMPK profiles, is orally available and well tolerated, and displayed tumor control in multiple in vivo studies of PAM pathway-driven tumors.

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.

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.

Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

Preparation method of docetaxel chiral side chain intermediate

The invention discloses a preparation method of a docetaxel chiral side chain intermediate. The method takes cheap and easily available L-phenylglycine 1 as a raw material, and the route is convenient to operate, good in stereoselectivity, mild in reaction condition, simple to separate and purify and relatively high in total yield, and can be used for large-scale preparation. The adopted raw materials are non-toxic, the production process is pollution-free and environment-friendly, and good conditions are created for industrial large-scale production and commercialization of the product.

Preparation method of (S)-4-phenyl-2-oxazolidinone

The invention discloses a preparation method for synthesizing (S)-4-phenyl-2-oxazolidinone, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: reducing N-Boc-L-phenylglycine with a borane reagent to obtain N-Boc-L-phenylglycinol, and carrying out a ring closing reaction under the action of a catalyst to obtain (S)-4-phenyl-2-oxazolidinone. The product reacts with sulfur powder and ammonium sulfide or ammonium polysulfide to obtain (S)-4-phenyl oxazolidine-2-thioketone. The method avoids the use of cytotoxic reagents or solvents, has the advantages of accessible raw materials, simple operation and the like, conforms to green chemistry, and has potential industrial amplification prospects.

COMPLEMENT MODULATORS AND RELATED METHODS

The present disclosure presents compounds and compositions that interact with complement components. Some compounds inhibit complement activity. Included are small molecule compounds and compositions that function as C5 inhibitor compounds. Methods for inhibiting complement activity and methods of treating complement-related indications with the C5 inhibitor compounds and compositions are provided.