129940-50-7

Basic information

• Product Name: (S)-(-)-Trityl glycidyl ether
• Synonyms: (S)-(-)-TRITYL GLYCIDYL ETHER;(S)-TRITYL GLYCIDYL ETHER;(S)-(-)-GLYCIDYL TRIPHENYLMETHYL ETHER;(S)-GLYCIDYL TRIPHENYLMETHYL ETHER;(S)-(-)-GLYCIDYL TRITYL ETHER;(S)-GLYCIDYL TRITYL ETHER;(S)-2,3-EPOXY-1-PROPYL TRIPHENYLMETHYL ETHER;(S)-2-(TRIPHENYLMETHOXYMETHYL)OXIRANE
• CAS NO: 129940-50-7
• Molecular Formula: C₂₂H₂₀O₂
• Molecular Weight: 316.39
• Product Categories: chiral;Heterocyclic Compounds;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Building Blocks;Epoxides;Organic Building Blocks
• Mol File: 129940-50-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 99-102 °C(lit.)
• Boiling Point: 438.8 °C at 760 mmHg
• Flash Point: 164.8 °C
• Appearance: white to light yellow crystal powder
• Density: 1.146 g/cm³
• Vapor Pressure: 1.73E-07mmHg at 25°C
• Refractive Index: -11 ° (C=1, CHCl3)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: almost transparency in hot Methanol
• CAS DataBase Reference: (S)-(-)-Trityl glycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Trityl glycidyl ether(129940-50-7)
• EPA Substance Registry System: (S)-(-)-Trityl glycidyl ether(129940-50-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 129940-50-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(-)-Glycidyl trityl ether may be used to prepare N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acid analogs, which are potent prostaglandin D2 (PGD2) receptor antagonists. It may also be used as a starting material in the multi-step synthesis of (-)-actisonitrile.

InChI:InChI=1/C22H20O2/c1-4-10-18(11-5-1)22(24-17-21-16-23-21,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,21H,16-17H2

Upstream product

• 60-29-7 diethyl ether 
• 556-52-5 oxiranyl-methanol 
• 76-83-5 trityl chloride 
• 60456-23-7 (S)-oxiranemethanol 
• 65291-30-7 trityl glycidyl ether 
• 124-38-9 carbon dioxide 
• 203250-06-0 (R)-3-chloro-1-O-trityl-1,2-propanediol 
• 57044-25-4 (R)-oxiranemethanol 
• 1235-22-9 allyl trityl ether 

Downstream Products

• 132336-34-6 (S)-N₁-[2-hydroxy-3-(triphenylmethoxy)propyl]-N₄-benzoylcytosine 
• 1025956-99-3 (2'S)-2-<(2'-hydroxy-3'-trityloxypropyl)amino>-2-(hydroxymethyl)propane-1,3-diol 
• 85550-19-2 (S)-1-triphenylmethoxypropan-2-ol 
• 170277-82-4 (2S)-1-triphenylmethoxy-4-pentene-2-ol 
• 303014-78-0 6-amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-7H-purin-8(9H)-one 
• 87888-87-7 6-amino-9-[(RS)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-7H-purin-8(9H)-one 
• 400864-57-5 9-[((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-8-{[(R)-2-hydroxy-3-(trityloxy)propyl]sulfanyl}adenine 
• 402575-67-1 (S)-1-(2-Amino-6-cyclopropylamino-purin-9-yl)-3-trityloxy-propan-2-ol 
• 2426-08-6 glycidyl n-butyl ether 
• 519-73-3 triphenylmethane 
• 785805-47-2 N-(2,4-difluorophenyl)-N-[(2S)-3-triphenylmethyloxy-2-hydroxypropyl]-4-methylbenzenesulfonamide 
• 55559-86-9 (S)-1-(6-amino-9H-purin-9-yl)-3-(trityloxy)propan-2-ol 
• 933460-54-9 1-[(2S)-2-hydroxy-3-(triphenylmethoxy)propyl]-5-azacytosine 
• 933460-55-0 1-[(2S)-2-hydroxy-3-(triphenylmethoxy)propyl]-6-azacytosine 

Relevant articles and documents

Divergent asymmetric total synthesis of all four pestalotin diastereomers from (R)-glycidol

All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asymmetric Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal der

Diastereoselective Desymmetrization of p-Quinamines through Regioselective Ring Opening of Epoxides and Aziridines

A highly diastereoselective desymmetrization of p-quinamines via regioselective ring opening of epoxides and aziridines under mild conditions has been developed. A chairlike six-membered transition state with minimized 1,3-diaxial interactions explains the relative stereoselectivity of the cyclization reaction. This transition-metal free [3 + 3] annulation reaction provides rapid access to fused bicyclic morpholines and piperazines with a tetrasubstituted carbon center in high yields. In addition, it also allows the synthesis of enantioenriched products by using easily accessible chiral nonracemic epoxides and aziridines.

Modular synthesis of dihydroxyacetone monoalkyl ethers and isosteric 1-hydroxy-2-alkanones

Straightforward methods for the efficient, systematic preparation of libraries of the title compound classes have been evaluated. A general and efficient modular route to dihydroxyacetone monoethers was developed based on trityl glycidol, which, through epoxide opening, oxidation, and deprotection, provided variously alkylated ethers by three routine operations in good overall yields (eight examples, 24-59 %). The preparation of structurally related 1-hydroxyalkanones depends on the availability of the most economic starting materials and on their physicochemical properties. Thus, the most practical one-step approaches consisted of the sec-selective oxidation of short-chain 1,2-diols (≤ C6) using NaOCl, and the direct ketohydroxylation of 1-alkenes (≥ C6) using buffered stoichiometric KMnO4 or catalytic RuO4 with reoxidation by oxone, for which mostly good overall yields were achieved on a multigram scale (nine examples, 15-78 %).