40435-14-1

Basic information

• Product Name: (S)-(+)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE
• Synonyms: (S)-(+)-2-HYDROXY-2-PHENYLETHYL P-TOLUENESULFONATE;(S)-(+)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE;(S)-(+)-1-PHENYLETHANEDIOL 2-TOSYLATE;(S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate, 98+%;(S)-(+)-2-Hydroxy-2-phenylethyl 4-methylbenzenesulfonate;(S)-1-Phenyl-1,2-ethanediol 2-Tosylate,99%e.e.
• CAS NO: 40435-14-1
• Molecular Formula: C₁₅H₁₆O₄S
• Molecular Weight: 292.35
• Product Categories: Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 40435-14-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 74-76 °C(lit.)
• Boiling Point: 480.6°Cat760mmHg
• Flash Point: 244.5°C
• Appearance: /
• Density: 1.274g/cm³
• Vapor Pressure: 4.77E-10mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.95±0.20(Predicted)
• CAS DataBase Reference: (S)-(+)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(40435-14-1)
• EPA Substance Registry System: (S)-(+)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(40435-14-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 40435-14-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

(S)-(+)-1-Phenylethane-1,2-diol 2-tosylate is an intermediate in the synthesis of (S)-Mirabegron (M364895), which is an impurity of Mirabegron (M364900). Mirabegron is a potent bladder relaxant and reagent for diabetes remedy.

InChI:InChI=1/C15H16O4S/c1-12-7-9-14(10-8-12)20(17,18)19-11-15(16)13-5-3-2-4-6-13/h2-10,15-16H,11H2,1H3/t15-/m1/s1

Upstream product

• 96-09-3 styrene oxide 
• 104-15-4 toluene-4-sulfonic acid 
• 93-56-1 phenylethane 1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 
• 856900-03-3 carbonic acid tert-butyl ester 2-hydroxy-1-phenyl-ethyl ester 
• 13704-09-1 (S)-(-)-ethyl mandelate 
• 40434-87-5 toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 17199-29-0 L-(+)-mandelic acid 
• 105581-82-6 (S)-2-(benzyloxy)-2-phenyl-1-ethanol 
• 20780-53-4 (R)-Styrene oxide 

Downstream Products

• 16162-51-9 (S)-(-)-(2-hydroxy-2-phenyl-1-ethyl)-phenyl thioether 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 124718-87-2 2-azido-1-phenylethan-1-ol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 14467-53-9 (S)-(+)-2-(-amino)-1-phenylethanol 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 865860-14-6 acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester 
• 865860-10-2 methyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranosyl-(1->3)-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside 
• 865859-90-1 3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate 
• 865860-08-8 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-galactopyranosyl trichloroacetimidate 

Relevant articles and documents

Chiral guanidine catalyzed acylative kinetic resolution of racemic 2-bromo-1-arylethanols

In this study, chiral guanidine catalyzed acylative kinetic resolution of racemic 2-bromo-1-arylethanols was achieved with high selectivity. Irrespective of the electronic nature and the substitution patterns on the aromatic rings, a variety of substrates were suitable for this reaction. The branched acyl component was considered to be optimal for obtaining high s-values. The transition state of the reaction was proposed based on the absolute configuration of the obtained product.

Diversity and oriented synthesis of clopidogrel drug derivatives

An efficient synthetic route has been developed for the synthesis of new clopidogrel drug derivatives. Key step of this method is to replacement of mesyl protected alcohol group with various aliphatic amines in presence of base. Various clopidogrel drug d

Development of novel LP1-based analogues with enhanced delta opioid receptor profile

Pain relief achieved by co-administration of drugs acting at different targets is more effective than that obtained with conventional MOR selective agonists usually associated to relevant side effects. It has been demonstrated that simultaneously targeting different opioid receptors is a more effective therapeutic strategy. Giving the promising role for DOR in pain management, novel LP1-based analogues with different N-substituents were designed and synthesized with the aim to improve DOR profile. For this purpose, we maintained the phenyl ring in the N-substituent of 6,7-benzomorphan scaffold linked to an ethyl spacer bearing a hydroxyl/methyl or methoxyl group at carbon 2 or including it in a 1,4-benzodioxane ring. LP1 analogues were tested by competition binding assays. Compounds 6 (KiMOR = 2.47 nM, KiDOR = 9.6 nM), 7 (KiMOR = 0.5 nM and KiDOR = 0.8 nM) and 9 (KiMOR = 1.08 nM, KiDOR = 6.6 nM) retained MOR affinity but displayed an improved DOR binding capacity as compared to LP1 (KiMOR = 0.83 nM, KiDOR = 29.1 nM). Moreover, GPI and MVD functional assays indicated that compounds 6 (IC50 = 49.2 and IC50 = 10.8 nM), 7 (IC50 = 9.9 and IC50 = 11.8 nM) and 9 (IC50 = 21.5 and IC50 = 4.4 nM) showed a MOR/DOR agonist profile, unlike LP1 that was a MOR agonist/DOR antagonist (IC50 = 1.9 and IC50 = 1240 nM). Measurements of their antinociceptive effect was evaluated by mice radiant tail flick test displaying for compounds 6, 7 and 9 ED50 values of 1.3, 1.0 and 0.9 mg/kg, i.p., respectively. Moreover, the antinociceptive effect of compound 9 was longer lasting with respect to LP1. In conclusion the N-substituent nature of compounds 6, 7 and 9 shifts the DOR profile of LP1 from antagonism to agonism.