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
• Article Data: 17

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

General Description

(S)-(-)-N-Boc-2-Amino-1,5-pentanediol, also known as N-tert-Butoxycarbonyl-2-amino-1,5-pentanediol, is a chiral compound commonly used in organic synthesis and pharmaceutical research. This chemical is a derivative of 2-amino-1,5-pentanediol with a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom, which provides stability and control during reactions. It is used as a building block for the synthesis of various biologically active compounds, such as amino alcohols and peptides, due to its ability to introduce chirality into molecules. (S)-(-)-N-Boc-2-Amino-1,5-pentanediol is also utilized as a chiral auxiliary in asymmetric synthesis and as a ligand in asymmetric catalysis, making it an important tool in the development of new pharmaceuticals and fine chemicals.

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

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

Downstream Products

• 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 
• 1395408-53-3 (S)-1-(1-benzylpiperidine-3-yl)-3-[3,5-bis(trifluoromethyl)phenyl]thiourea 
• 1395408-55-5 (S)-1-(1-methylpiperidine-3-yl)-3-phenylthiourea 
• 1395408-56-6 (S)-1-(1-methylpiperidine-3-yl)-3-p-tolylthiourea 
• 1395408-57-7 (S)-1-(1-methylpiperidine-3-yl)-3-[4-(trifluoromethyl)phenyl]thiourea 
• 1395408-58-8 (S)-1-(1-methylpiperidine-3-yl)-3-(4-nitrophenyl)thiourea 
• 1395408-59-9 (S)-1-(4-chlorophenyl)-3-(1-methylpiperidine-3-yl)thiourea 
• 1395408-60-2 (S)-1-(3,5-dichlorophenyl)-3-(1-methylpiperidine-3-yl)thiourea 
• 1395408-61-3 (S)-1-(4-fluorophenyl)-3-(1-methylpiperidine-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.

Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation

A convenient approach towards the synthesis of orthogonally protected chiral bis-a-amino acids (OPBAAs) is described. The key transformations include: (1) a highly stereoselective conjugation (alkylation) of the Sch?llkopf bislactim ethers and oxazolidinyl alkyl halides to build a backbone skeleton; and (2) our orthogonal protection strategy. A series of enantiopure OPBAAs bearing a variety of alkyl chain as a spacer; two stereogenic centers; and three protecting groups were prepared as examples. These versatile molecules were applied to the synthesis of biologically interesting di- or tri-peptide analogues, including chiral iE-meso-DAP and A-iE-meso-DAP, for the study of Nod1 activation in the innate immune response.

TRICYCLIC HETEROCYCLIC COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF AS JAK INHIBITORS

The invention provides novel compounds of formula I having the general formula:(I) wherein Rl s R2, R3, X and Y are as described herein. Accordingly, the compounds may be provided in pharmaceutically acceptable compositions and used for the treatment of immunological or hyperproliferative disorders.