14618-80-5 Usage
Description
(R)-(-)-Benzyl glycidyl ether is an organic compound that is commonly utilized as an intermediate in the synthesis of various pharmaceuticals and chemical products. It is characterized by its colorless to light yellow liquid appearance and possesses a reactive epoxide group, which allows it to participate in numerous chemical reactions.
Uses
Used in Pharmaceutical Industry:
(R)-(-)-Benzyl glycidyl ether is used as a key intermediate for the preparation of the lactone fragment of compactin and mevinolin. These compounds are important in the development of cholesterol-lowering drugs, as they serve as inhibitors of HMG-CoA reductase, a key enzyme in cholesterol synthesis.
Used in Chemical Synthesis:
(R)-(-)-Benzyl glycidyl ether is used as a reactant in the synthesis of syn-1,3-polyols, which are valuable building blocks in organic chemistry. These polyols can be further transformed into various chemical products, such as dideoxynucleosides and spiroacetal cyanohydrins, which have applications in the fields of pharmaceuticals, agrochemicals, and materials science.
Used in Suzuki-Miyaura Coupling Reaction:
(R)-(-)-Benzyl glycidyl ether can be employed in the Suzuki-Miyaura coupling reaction to synthesize pyrazole derivatives by reacting with different aryl halides over a palladium catalyst. This reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules and pharmaceuticals.
Synthesis Reference(s)
Tetrahedron Letters, 21, p. 4807, 1980 DOI: 10.1016/0040-4039(80)80145-6
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 14618-80-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,1 and 8 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 14618-80:
(7*1)+(6*4)+(5*6)+(4*1)+(3*8)+(2*8)+(1*0)=105
105 % 10 = 5
So 14618-80-5 is a valid CAS Registry Number.
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
14618-80-5Relevant articles and documents
A TWO-STEP SYNTHESIS OF (R)- AND (S)-BENZYLGLYCIDYL ETHER
Byun, Hoe-Sup,Bittman, Robert
, p. 2751 - 2754 (1989)
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
Gurjar,Sarma,Sadalapure,Adhikari
, p. 1424 - 1424 (1998)
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
Bendigiri, Chandrika,Harini,Yenkar, Sajal,Zinjarde, Smita,Sowdhamini,Ravikumar, Ameeta
, p. 12918 - 12926 (2018)
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
Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
supporting information, p. 18039 - 18042 (2021/11/16)
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.
Stereoselective total synthesis of (?)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization
Rahman, Md. Ataur,Haque, Ashanul,Yadav, Jhillu Singh
, (2020/07/03)
The stereoselective total synthesis of (?)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.
