14618-80-5

Basic information

• Product Name: (R)-(-)-Benzyl glycidyl ether
• Synonyms: (R)-(-)-BENZYL GLYCIDYL ETHER;(R)-BENZYL GLYCIDYL ETHER;(R)-BENZYLOXYMETHYL-OXIRANE;RARECHEM AK HZ 0049;(R)-(-)-2-(BENZYLOXYMETHYL)OXIRANE;(R)-(-)-1-BENZYLOXY-2,3-EPOXYPROPANE;(R)-1-BENZYLOXY-2,3-EPOXYPROPANE;(r)-o-benzylglycidol
• CAS NO: 14618-80-5
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 220-899-5
• Product Categories: chiral;API intermediates;CHIRAL COMPOUNDS;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound
• Mol File: 14618-80-5.mol
• Article Data: 100

Chemical Properties

• Melting Point: 88-93°C
• Boiling Point: 130 °C (0.1 mmHg)
• Flash Point: >230 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.077 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0303mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water.
• BRN: 3588399
• CAS DataBase Reference: (R)-(-)-Benzyl glycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Benzyl glycidyl ether(14618-80-5)
• EPA Substance Registry System: (R)-(-)-Benzyl glycidyl ether(14618-80-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: TX2860020
• Hazardous Substances Data: 14618-80-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Used in the preparation of the lactone fragment of compactin and mevinolin. Chiron in the preparation of syn-1,3-polyols, dideoxynucleosides, and a spiroacetal cyanohydrin.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 4807, 1980 DOI: 10.1016/0040-4039(80)80145-6

General Description

1H-Pyrazol-3-ylboronic acid hydrate can be used as a reactant in the Suzuki-Miyaura coupling reaction to synthesize pyrazole derivatives by reacting with different aryl halides over the palladium catalyst.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

This ether in EtOAc is dried (Na2SO4), then purified by flash chromatography using pet ether/EtOAc (5:1) as eluent. The ether distils through a short path distillation apparatus (Kügelrohr) as a colourless liquid. Alternatively, dissolve it in CHCl3, wash it with H2O, dry (Na2SO4), evaporate and purify by silica gel chromatography. [Anisuzzamen & Owen J Chem Soc 1021 1967, Takano et al. Heterocycles 1 6 381 1981, Lipshutz et al. Org Synth 69 82 1990, Takano et al. Synthesis 539 1989, Honda et al. Chem Pharm Bull Jpn 39 1385 1991, Beilstein 12 IV 2277.]

InChI:InChI=1/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2/t10-/m0/s1

Upstream product

• 14593-43-2 benzyl allyl ether 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 100-39-0 benzyl bromide 
• 78906-15-7 tert-butyldimethylsilyl (S)-glycidyl ether 
• 112497-11-7 (R)-1-Benzyloxy-3-p-tolylsulfanyl-propan-2-ol 
• 151715-97-8 (R)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 100-51-6 benzyl alcohol 
• 1122091-57-9 C₁₈H₂₂O₅S 
• 67843-74-7 (S)-epichlorohydrin 
• 124-38-9 carbon dioxide 
• 16495-04-8 (S)-1-O-benzyl-3-p-toluenesulfonyl-syn-glycerol 
• 60456-23-7 (S)-oxiranemethanol 

Downstream Products

• 392230-13-6 (2R)-1-benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol 
• 125782-68-5 (S)-1-Benzyloxy-3-(5-hydroxymethyl-furan-2-yl)-propan-2-ol 
• 85758-01-6 (R)-5-Benzyloxy-4-hydroxy-2-p-tolyl-pentanenitrile 
• 112497-12-8 (S)-1-Benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol 
• 83167-57-1 3-O-Benzyl-1-O-octadecyl-sn-glycerol 
• 150824-10-5 (S)-1-O-Benzyl-3-(mesitylthio)-1,2-propanediol 
• 93782-24-2 (5R)-5-<(benzyloxy)methyl>-3-isopropylidenetetrahydrofuran-2-one 
• 93782-25-3 (3R,5R)-5-<(benzyloxy)methyl>-3-isopropenyltetrahydrofuran-2-one 
• 93782-26-4 (-)-(3S,5R)-5-<(benzyloxy)methyl>-3-isopropenyltetrahydrofuran-2-one 
• 93782-22-0 (R)-5-Benzyloxy-4-hydroxy-2-isopropylidene-pentanoic acid 
• 145308-75-4 (S)-1-benzyloxy-4-decyn-2-ol 
• 137819-95-5 (2R)-1-Benzyloxydec-4-yn-2-ol 
• 83287-36-9 (R)-5-Benzyloxy-4-hydroxy-2-(3-methoxy-phenyl)-pentanenitrile 
• 164515-26-8 (2S)-1-(2'-benzyloxyphenoxy)-3-benzyloxy-2-propanol 

Relevant articles and documents

A TWO-STEP SYNTHESIS OF (R)- AND (S)-BENZYLGLYCIDYL ETHER

Ring opening of (R)- and (S)-glycidyl tosylates with benzyl alcohol, followed by treatment with K2CO3/MeOH gave (S)-(+)- and (R)-(-)-benzylglycidyl ether in 90percent overall yield.

A practical synthesis of (R)- and (S)-benzylglycidols by hydrolytic kinetic resolution

A new synthetic approach to both the enantiomers of O-benzylglycidol, involving hydrolytic kinetic resolution, has been described.

Evaluating Ylehd, a recombinant epoxide hydrolase from: Yarrowia lipolytica as a potential biocatalyst for the resolution of benzyl glycidyl ether

Glycidyl ethers and their vicinal diols are important building blocks in the organic synthesis of anti-cancer and anti-obesity drugs. Ylehd, an epoxide hydrolase from tropical marine yeast Yarrowia lipolytica, was explored for its enantioselective propert

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.