(R)-Glycidyl tosylate

Base Information

• Chemical Name: (R)-Glycidyl tosylate
• CAS No.: 113826-06-5
• Molecular Formula: C10H12O4S
• Molecular Weight: 228.269
• Hs Code.: 29109000
• UNII: 62V982IWII
• DSSTox Substance ID: DTXSID00150574
• Nikkaji Number: J534.804H
• Wikidata: Q27893760
• Mol file: 113826-06-5.mol

Synonyms:(2R)-glycidyl tosylate;(2S)-glycidyl tosylate;glycidyl tosylate

Chemical Property of (R)-Glycidyl tosylate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.35E-05mmHg at 25°C
• Melting Point: 45-48 °C
• Refractive Index: 1.55
• Boiling Point: 370.5 °C at 760 mmHg
• Flash Point: 177.9 °C
• PSA: 64.28000
• Density: 1.31g/cm³
• LogP: 2.17990
• Storage Temp.: 2-8°C
• Solubility.: dioxane: 50 mg/mL, clear
• Water Solubility.: decomposes
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 228.04563003
• Heavy Atom Count: 15
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

(2R)-(?)-Glycidyl tosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T
• Hazard Codes: Xn,N,T
• Statements: 45-41-43-51/53-68
• Safety Statements: 61-45-36/37/39-26-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CO2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CO2
• Uses: Protected Glycidol, (2R)-(-)-Glycidyl tosylate is used as an intermediate in the preparation of neurochemicals. (2R)-(-)-Glycidyl Tosylate is a protected glycidol used as an intermediate in the preparation of neurochemicals. (2R)-(-)-Glycidyl tosylate may be used to prepare:1-O-hexadecyl-sn-glycerol 3-O-p-toluenesulfonate by reacting with 1-hexadecanol in the presence of boron trifluoride etherate. 4-Oxiranylmethoxy-(1H)-indole by reacting with 4-hydroxyindole in the presence of sodium hydride.[18F]Epifluorohydin, an intermediate for preparing of [18F]fluoromisonidazole.It can also be used as a starting material in the synthesis of 1,2-diacyl-sn-3-glycerophosphocholines.

Technology Process of (R)-Glycidyl tosylate

There total 5 articles about (R)-Glycidyl tosylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

→ (R)-glycidyl tosylate (113826-06-5,6746-81-2)

Guidance literature:

Reference yield: 95.0%

p-toluenesulfonyl chloride (98-59-9) + (S)-oxiranemethanol (60456-23-7) → (R)-glycidyl tosylate (113826-06-5,6746-81-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4cc02702g

Reference yield:

oxiranyl-methanol (556-52-5) + p-toluenesulfonyl chloride (98-59-9) → (R)-glycidyl tosylate (113826-06-5,6746-81-2) + (S)-Glycidyl tosylate (70987-78-9,6746-81-2)

Guidance literature:

oxiranyl-methanol; With zinc trifluoromethanesulfonate; (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole); In dichloromethane; for 0.333333h; Inert atmosphere;

p-toluenesulfonyl chloride; With potassium carbonate; In dichloromethane; at 20 ℃; for 17h;

In ethanol; hexan-1-ol; Reagent/catalyst; Solvent; Overall yield = 54 %; Resolution of racemate;

upstream raw materials:

allyl alcohol

p-toluenesulfonyl chloride

(S)-oxiranemethanol

oxiranyl-methanol

Downstream raw materials:

4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine

4-{4-[(2R)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine

Toluene-4-sulfonic acid (R)-3-(16-chloro-hexadecyloxy)-2-hydroxy-propyl ester

Toluene-4-sulfonic acid (S)-2-hydroxy-nonyl ester

Refernces

• 1、 Breunig, Michael,Gaich, Tanja,Yuan, Po. "An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5". supporting information. p. 5521 - 5525. Retrieved 2020/02/20.
• 2、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.