70987-78-9

Basic information

• Product Name: (2S)-(+)-Glycidyl tosylate
• Synonyms: (S)-Glycidil Tosylate;(S)-Oxiran-2-ylMethyl 4-Methylbenzenesulfonate;(2S)-2-OxiraneMethanol 2-(4-Methylbenzenesulfonate);(S)-(2,3-Epoxypropan-1-yl) 4-Methylbenzenesulfonate;(S)-Oxiran-2-ylMethyl Toluene-4-sulfonate;(S)-Toluene-4-sulfonic Scid OxiranylMethyl Ester;(2S)-(+)-Glycidyl Tosylate p-Toluenesulfonic Acid (2S)-(+)-Glycidyl Ester;(S)-Glycidyl toluene-4-sulphonate
• CAS NO: 70987-78-9
• Molecular Formula: C₁₀H₁₂O₄S
• Molecular Weight: 228.26
• EINECS: 417-210-7
• Product Categories: Carbohydrates & Derivatives;Sulfur & Selenium Compounds;Phenyls & Phenyl-Het;chiral;CHIRAL COMPOUNDS;Chiral Compound;Phenyls & Phenyl-Het;Aromatics
• Mol File: 70987-78-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 340.07°C (rough estimate)
• Flash Point: >230 °F
• Appearance: White/Fluffy Powder
• Density: 1.3749 (rough estimate)
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility: decomposes
• BRN: 3592143
• CAS DataBase Reference: (2S)-(+)-Glycidyl tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(+)-Glycidyl tosylate(70987-78-9)
• EPA Substance Registry System: (2S)-(+)-Glycidyl tosylate(70987-78-9)

Safety Data

• Hazard Codes: T,N,Xi
• Statements: 45-41-43-51/53-68
• Safety Statements: 53-45-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: RR0510050
• F: 3-10-21
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 70987-78-9(Hazardous Substances Data)

Usage

Description

(2S)-(+)-Glycidyl tosylate is a chiral epoxide compound that serves as a protected form of glycidol. It is characterized by its specific stereochemistry, with the (2S) configuration and a positive optical rotation, making it a valuable intermediate in the synthesis of various organic compounds.

Uses

Used in the Pharmaceutical Industry:
(2S)-(+)-Glycidyl tosylate is used as an intermediate in the preparation of neurochemicals, which are essential for the development and functioning of the nervous system. Its chiral nature allows for the synthesis of enantiomerically pure compounds, which is crucial for the biological activity and selectivity of pharmaceutical agents.
Used in Organic Synthesis:
(2S)-(+)-Glycidyl tosylate is employed in the first enantioselective synthesis of (R)and (S)-4-acetyl-3-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b]oxazines. These compounds have potential applications in various fields, including pharmaceuticals and materials science, due to their unique structural features and properties. The use of (2S)-(+)-Glycidyl tosylate in this synthesis allows for the production of enantiomerically pure products, which is vital for their potential applications.

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/t9-/m0/s1

Upstream product

• 107-18-6 allyl alcohol 
• 98-59-9 p-toluenesulfonyl chloride 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 107-06-2 1,2-dichloro-ethane 
• 57044-25-4 (R)-oxiranemethanol 
• 556-52-5 oxiranyl-methanol 
• 118712-54-2 glycidyl p-toluenesulfonate 

Downstream Products

• 120019-37-6 3-hexadecyloxy-2R-hydroxypropyl 1-para-toluenesulphonate 
• 119944-30-8 3‐hexadecyloxy‐2R‐hydroxyl propyl‐1‐p‐toluene sulphonate 
• 146838-96-2 (S,S)-(-)-1-(1-Naphthyloxy)-2-hydroxy-3-N-(1-phenylethylamino)propane hydrochloride 
• 146838-98-4 (S,R)-1-(1-Naphthyloxy)-2-hydroxy-3-N-(1-phenylethylamino)propane hydrochloride 
• 136404-80-3 (S)-1-azido-2-trimethylsilyloxy-3-tosyloxypropane 
• 136404-79-0 (R)-1-azido-2-trimethylsilyloxy-3-tosyloxypropane 
• 145987-94-6 (2S)-2-hydroxy-6-(trimethylsilyl)-4-hexynyl tosylate 
• 68051-01-4 (2S)-3-(4-acetamidophenoxy)-1,2-epoxypropane 
• 144604-85-3 (2S,4RS)-2-hydroxy-4-phenylsulfonyl-5-trimethylsilyl-1-pentyl p-toluenesulfonate 
• 160961-51-3 (S)-4-isobutoxycarbonylphenoxy-2,3-epoxypropane 
• 132059-11-1 R-<1-(2-amino-3-nitrophenoxy)>-2',3'-epoxypropane 
• 132059-13-3 S-<1-(2-amino-3-nitrophenoxy)>-2',3'-epoxypropane 
• 151837-96-6 (2S)-1-(p-toluenesulphonyloxy)-4-(4-chlorophenyl)butan-2-ol 
• 158380-44-0 (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(R)-oxiranyl-propan-1-one 

Relevant articles and documents

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

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.

Chiral ND - 322, ND - 364 or ND - 364 sulfoxide analogs and its preparation method

The invention relates to a chiral ND-322, ND-364 or ND-364 sulfoxide analog and a preparation method therefor, and belongs to the technical field of pharmaceutical active compound synthesis. The chiral ND-322, ND-364 or ND-364 sulfoxide analog takes chira

Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence

The total synthesis of (+)-cryptocaryol A was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogeni