162955-48-8

Basic information

• Product Name: (S)-(-)-N-Boc-2-Amino-1,5-pentanediol
• Synonyms: (S)-(-)-N-Boc-2-Amino-1,5-pentanediol
• CAS NO: 162955-48-8
• Molecular Formula: C₁₀H₂₁NO₄
• Molecular Weight: 219.27804
• Mol File: 162955-48-8.mol

Chemical Properties

• Boiling Point: 399 °C at 760 mmHg
• Flash Point: 195.1 °C
• Appearance: /
• Density: 1.089 g/cm³
• Vapor Pressure: 5.02E-08mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: (S)-(-)-N-Boc-2-Amino-1,5-pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N-Boc-2-Amino-1,5-pentanediol(162955-48-8)
• EPA Substance Registry System: (S)-(-)-N-Boc-2-Amino-1,5-pentanediol(162955-48-8)

Safety Data

• Hazardous Substances Data: 162955-48-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
(S)-(-)-N-Boc-2-Amino-1,5-pentanediol is used as a building block for the synthesis of biologically active compounds, such as amino alcohols and peptides, due to its ability to introduce chirality into molecules. This chirality is crucial for the development of new pharmaceuticals, as it can lead to more effective and selective drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-(-)-N-Boc-2-Amino-1,5-pentanediol is employed as a chiral auxiliary, which helps in the synthesis of enantiomerically pure compounds. This is important for the production of high-quality fine chemicals and pharmaceutical intermediates.
Used in Asymmetric Synthesis:
(S)-(-)-N-Boc-2-Amino-1,5-pentanediol is utilized as a chiral auxiliary in asymmetric synthesis, a technique that allows for the selective formation of one enantiomer over another. This is particularly valuable in the production of enantiomerically pure compounds, which are often required for pharmaceutical applications.
Used in Asymmetric Catalysis:
As a ligand in asymmetric catalysis, (S)-(-)-N-Boc-2-Amino-1,5-pentanediol plays a critical role in the development of new catalysts that can selectively produce one enantiomer of a compound. This selective synthesis is essential for creating pharmaceuticals with specific biological activities and reducing potential side effects caused by the unwanted enantiomer.

InChI:InChI=1/C10H21NO4/c1-10(2,3)15-9(14)11-8(7-13)5-4-6-12/h8,12-13H,4-7H2,1-3H3,(H,11,14)/t8-/m0/s1

Upstream product

• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 130696-54-7 diethyl (tert-butoxycarbonyl)-L-glutamate 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 56-86-0 L-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 4931-66-2 methyl (S)-pyroglutamate 
• 2419-94-5 Boc-Glu 

Downstream Products

• 136923-04-1 tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 216854-23-8 tert-butyl (S)-piperidin-3-yl-carbamate 
• 216854-24-9 tert-butyl (S)-(N-benzylpiperidin-3-yl)carbamate 
• 1294006-96-4 C₃₁H₄₁N₃O₅ 
• 84590-48-7 indolactam V 
• 1361323-26-3 tert-butyl (S)-1-cyclohexyl-2-oxo-2-((S)-1-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-3-ylamino)ethylcarbamate 
• 1361323-28-5 tert-butyl (S)-1-((S)-1-cyclohexyl-2-oxo-2-((S)-1-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-3-ylamino)ethylamino)-1-oxopropan-2-yl(methyl)carbamate 
• 1361322-59-9 (S)-N-((S)-1-cyclohexyl-2-oxo-2-((S)-1-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-3-ylamino)ethyl)-2-(methylamino)propanamide 
• 1395408-71-5 (S)-N-(1-methylpiperidine-3-yl)-P,P-diphenylphosphinthioic amide 
• 1395408-72-6 (S)-N-(1-methylpiperidine-3-yl)-3,5-bis(trifluoromethyl)benzenesulfonamide 
• 1395408-49-7 (S)-1-[3,5-bis(trifluoromethyl)phenyl]-3-(1-methylpiperidine-3-yl)thiourea 
• 1395408-50-0 (S)-1-[3,5-bis(trifluoromethyl)phenyl]-3-(1-isopropylpiperidine-3-yl)thiourea 
• 1395408-51-1 (S)-1-[3,5-bis(trifluoromethyl)phenyl]-3-(1-tert-butylpiperidine-3-yl)thiourea 
• 1395408-52-2 (S)-1-[3,5-bis(trifluoromethyl)phenyl]-3-(1-cyclohexylpiperidine-3-yl)thiourea 

Relevant articles and documents

Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells

Human proteinase-activated receptor 2 (PAR2), a transmembrane G-protein-coupled receptor (GPCR), is an attractive target for a novel anticancer therapy, as it plays a critical role in cell migration and invasion. Selective PAR2 inhibitors therefore have potential as anti-metastatic drugs. Knowing that the natural product teleocidin A2 is able to inhibit PAR2 in tumor cells, the goal of the present study was to elaborate structure–activity relationships and to identify potent PAR2 inhibitors with lower activity against the adverse target, protein kinase C (PKC). For this purpose, an efficient gram-scale total synthesis of indolactam V (i.e., the parent structure of all teleocidins) was developed, and a library of derivatives was prepared. Some compounds were indeed found to exhibit high potency as PAR2 inhibitors at low nanomolar concentrations with improved selectivity (relative to teleocidin A2). The pseudopeptidic fragment bridging the C3 and C4 positions of the indole core proved to be essential for target binding, whereas activity and target selectivity depends on the substituents at N1 or C7. This study revealed novel derivatives that show high efficacy in PAR2 antagonism combined with increased selectivity.

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