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(2R)-(-)-Glycidyl tosylate is a white crystalline powder that serves as a protected glycidol and is widely utilized as an intermediate in the synthesis of various compounds, particularly in the field of neurochemistry.

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  • 113826-06-5 Structure
  • Basic information

    1. Product Name: (2R)-(-)-Glycidyl tosylate
    2. Synonyms: (2R)-GLYCIDYL TOLUENESULFONATE;(2R)-(-)-GLYCIDYL TOSYLATE;(2R)-OXIRAN-2-YLMETHYL 4-METHYLBENZENESULPHONATE;(2R)-(-)-TOLUENE-4-SULFONIC ACID 2,3-EPOXYPROPYL ESTER;LABOTEST-BB LT00440878;OXIRANEMETHANOL, 4-METHYLBENZENESULFONATE, (2R)-;(S)-Oxiranemethanol 4-methylbenzenesulfonate;(R)-(-)-OXIRANE-2-METHANOL 4-TOLUENESULFONATE
    3. CAS NO:113826-06-5
    4. Molecular Formula: C10H12O4S
    5. Molecular Weight: 228.26
    6. EINECS: 205-970-0
    7. Product Categories: chiral;API intermediates;Chiral Compound;Ring Systems;Aromatics;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
    8. Mol File: 113826-06-5.mol
  • Chemical Properties

    1. Melting Point: 46-49 °C(lit.)
    2. Boiling Point: 340.07°C (rough estimate)
    3. Flash Point: >230 °F
    4. Appearance: yellow to orange/powder
    5. Density: 1.3749 (rough estimate)
    6. Vapor Pressure: 2.35E-05mmHg at 25°C
    7. Refractive Index: 1.5400 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: dioxane: 50 mg/mL, clear
    10. Water Solubility: decomposes
    11. BRN: 3592142
    12. CAS DataBase Reference: (2R)-(-)-Glycidyl tosylate(CAS DataBase Reference)
    13. NIST Chemistry Reference: (2R)-(-)-Glycidyl tosylate(113826-06-5)
    14. EPA Substance Registry System: (2R)-(-)-Glycidyl tosylate(113826-06-5)
  • Safety Data

    1. Hazard Codes: Xn,N,T
    2. Statements: 45-41-43-51/53-68
    3. Safety Statements: 61-45-36/37/39-26-53
    4. RIDADR: UN 3077 9/PG 3
    5. WGK Germany: 3
    6. RTECS: RR0510000
    7. F: 3-10-21
    8. HazardClass: 9
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 113826-06-5(Hazardous Substances Data)

113826-06-5 Usage

Uses

Used in Pharmaceutical Industry:
(2R)-(-)-Glycidyl tosylate is used as an intermediate for the preparation of neurochemicals, which are essential for understanding and treating neurological disorders and conditions.
Used in Chemical Synthesis:
(2R)-(-)-Glycidyl tosylate is used as a starting material in the synthesis of various compounds, such as:
1. 1-O-hexadecyl-sn-glycerol 3-O-p-toluenesulfonate, which is prepared by reacting with 1-hexadecanol in the presence of boron trifluoride etherate.
2. 4-Oxiranylmethoxy-(1H)-indole, which is synthesized by reacting with 4-hydroxyindole in the presence of sodium hydride.
3. [18F]Epifluorohydin, an intermediate for preparing [18F]fluoromisonidazole, a radiotracer used in medical imaging.
4. 1,2-diacyl-sn-3-glycerophosphocholines, which are important components of cell membranes and have potential applications in the study of lipid metabolism and related diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 113826-06-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,3,8,2 and 6 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 113826-06:
(8*1)+(7*1)+(6*3)+(5*8)+(4*2)+(3*6)+(2*0)+(1*6)=105
105 % 10 = 5
So 113826-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3

113826-06-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • TCI America

  • (T1611)  (2R)-(-)-Glycidyl p-Toluenesulfonate  >98.0%(GC)

  • 113826-06-5

  • 5g

  • 690.00CNY

  • Detail
  • TCI America

  • (T1611)  (2R)-(-)-Glycidyl p-Toluenesulfonate  >98.0%(GC)

  • 113826-06-5

  • 25g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (H55774)  (2R)-(-)-Glycidyl p-toluenesulfonate, 99%   

  • 113826-06-5

  • 1g

  • 516.0CNY

  • Detail
  • Alfa Aesar

  • (H55774)  (2R)-(-)-Glycidyl p-toluenesulfonate, 99%   

  • 113826-06-5

  • 5g

  • 1158.0CNY

  • Detail
  • Alfa Aesar

  • (H55774)  (2R)-(-)-Glycidyl p-toluenesulfonate, 99%   

  • 113826-06-5

  • 25g

  • 3718.0CNY

  • Detail
  • Aldrich

  • (540110)  (2R)-(−)-Glycidyltosylate  98%

  • 113826-06-5

  • 540110-5G

  • 831.87CNY

  • Detail
  • Aldrich

  • (540110)  (2R)-(−)-Glycidyltosylate  98%

  • 113826-06-5

  • 540110-25G

  • 2,623.14CNY

  • Detail

113826-06-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R)-(-)-Glycidyl tosylate

1.2 Other means of identification

Product number -
Other names [(2R)-oxiran-2-yl]methyl 4-methylbenzenesulfonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:113826-06-5 SDS

113826-06-5Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong

, p. 1080 - 1090 (2020/05/25)

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5

Breunig, Michael,Gaich, Tanja,Yuan, Po

supporting information, p. 5521 - 5525 (2020/02/20)

We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. Ring-closing metathesis and an auxiliary-directed 1,4-addition are the key steps of our synthetic route. During the synthesis, an unprecede

Development of Selective Steroid Inhibitors for the Glucose-6-phosphate Dehydrogenase from Trypanosoma cruzi

Fredo Naciuk, Fabrício,Do Nascimento Faria, Jéssica,Gonc?lves Eufrásio, Amanda,Torres Cordeiro, Artur,Bruder, Marjorie

supporting information, p. 1250 - 1256 (2020/07/27)

Chagas disease is a parasitic infection affecting millions of people across Latin America, imposing a dramatic socioeconomic burden. Despite the availability of drugs, nifurtimox and benznidazole, lack of efficacy and incidence of side-effects prompt the identification of novel, efficient, and affordable drug candidates. To address this issue, one strategy could be probing the susceptibility of Trypanosoma parasites toward NADP-dependent enzyme inhibitors. Recently, steroids of the androstane group have been described as highly potent but nonselective inhibitors of parasitic glucose-6-phosphate dehydrogenase (G6PDH). In order to promote selectivity, we have synthesized and evaluated 26 steroid derivatives of epiandrosterone in enzymatic assays, whereby 17 compounds were shown to display moderate to high selectivity for T. cruzi over the human G6PDH. In addition, three compounds were effective in killing intracellular T. cruzi forms infecting rat cardiomyocytes. Altogether, this study provides new SAR data around G6PDH and further supports this target for treating Chagas disease.

Method for manufacturing optically active cyclic ether ester derivative

-

Paragraph 0100; 0101; 0102, (2017/01/02)

The invention provides a method for simply and selectively manufacturing an optically active cyclic ether aryl sulfonic acid ester with an inexpensively obtained racemate as the raw material. The method for manufacturing the cyclic ether aryl sulfonic acid ester comprises the steps of with the existence of optically active bisoxazoline ligand, lewis acid compound, alkali and organic solvent, aryl sulfonyl halide and hydroxymethyl cyclic ether are subjected to the racemate reaction to obtain an optically active cyclic ether aryl sulfonic acid ester. Preferably glycidyl or 2-hydroxymethyl tetrahydrofuran is adopted as the above hydroxymethyl cyclic ether.

Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase

Yan, Yugang,Chen, Xueying,Yang, Xinying,Zhang, Jian,Xu, Wenfang,Zhang, Yingjie

, p. 6632 - 6640 (2015/10/19)

Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)-

Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation-reductive cleavage sequence

Brun, Elodie,Bellosta, Véronique,Cossy, Janine

supporting information, p. 6718 - 6721 (2014/06/23)

Stereocontrolled and efficient access to all the diastereomers of 1,3,5,7-tetraol structural units was developed using a Prins cyclisation-reductive cleavage sequence applied to tetrahydropyran aldehydes. Furthermore, these tetraols can be selectively functionalized. This journal is the Partner Organisations 2014.

PROCESSES AND INTERMEDIATES FOR PREPARING RIVAROXABAN

-

Paragraph 0205; 0206, (2015/01/07)

The invention discloses processes for the preparation of rivaroxaban and its pharmaceutically acceptable salts, solvates, and hydrates thereof. The invention also relates to novel intermediates for the preparation of rivaroxaban.

Towards dual antithrombotic compounds-Balancing thrombin inhibitory and fibrinogen GPIIb/IIIa binding inhibitory activities of 2,3-dihydro-1,4- benzodioxine derivatives through regio- and stereoisomerism

Ilic, Milos,Dunkel, Petra,Ilas, Janez,Chabielska, Ewa,Zakrzeska, Agnieszka,Matyus, Peter,Kikelj, Danijel

, p. 329 - 340 (2013/05/22)

Enantiomers of 2,3-dihydro-1,4-benzodioxine derivatives possessing both thrombin and fibrinogen GPIIb/IIIa binding inhibitory activities were prepared from (R)- and (S)-glycidol as potential dual antithrombotic compounds. The influence of chirality and su

PROCESSES AND INTERMEDIATES FOR PREPARING RIVAROXABAN

-

Page/Page column 40-41, (2013/07/19)

The invention discloses processes for the preparation of rivaroxaban and its pharmaceutically acceptable salts, solvates, and hydrates thereof. The invention also relates to novel intermediates for the preparation of rivaroxaban.

PROCESS FOR THE PREPARATION OF GLYCIDYL DERIVATIVES

-

Page/Page column 8, (2008/06/13)

There is provided a process for preparing a glycidyl derivative from 3-chloro-1,2-propanediol, comprising i) adding a phosphate salt to a solution into which 3-chloro-1,2-propanediol is dissolved into a solvent to produce glycidol, and ii) adding to the solution of step i) a base capable of releasing a glycidyl group from the glycidol and a substrate susceptible to nucleophilic attack to produce the desired glycidyl derivative by nucleophilic attack of the glycidyl group to the substrate.

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