(R)-(-)-Benzyl glycidyl ether

Base Information

• Chemical Name: (R)-(-)-Benzyl glycidyl ether
• CAS No.: 14618-80-5
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 29109000
• European Community (EC) Number: 604-513-6
• DSSTox Substance ID: DTXSID10932782
• Nikkaji Number: J81.789I
• Wikidata: Q72441191
• Mol file: 14618-80-5.mol

Synonyms:14618-80-5;(r)-benzyloxymethyl-oxirane;(R)-(-)-Benzyl glycidyl ether;(R)-2-((Benzyloxy)methyl)oxirane;Benzyl (R)-(-)-Glycidyl Ether;(R)-Benzyl glycidyl ether;(R)-O-Benzylglycidol;(R)-(-)-Glycidyl benzyl ether;(2R)-2-(phenylmethoxymethyl)oxirane;(R)-(-)-2-(Benzyloxymethyl)oxirane;CCRIS 6385;(R)-2-(benzyloxymethyl)oxirane;(R)-(-)-Benzyloxymethyloxirane;(-)-Benzyl (R)-glycidyl ether;(R)-benzylglycidyl ether;(S)-1-(Benzyloxy)-2,3-epoxypropane;BRN 3588399;Oxirane, [(phenylmethoxy)methyl]-, (2R)-;(2R)-2-[(benzyloxy)methyl]oxirane;MFCD00068409;(R)-(-)-1-Benzyloxy-2,3-epoxypropane;Oxirane, ((phenylmethoxy)methyl)-, (R)-;Propane, 1-(benzyloxy)-2,3-epoxy-, (R)-;5-17-03-00016 (Beilstein Handbook Reference);(R)-2-[(benzyloxy)methyl]oxirane;(-)-Benzyl-(R)-glycidylether;Propane, 1-(benzyloxy)-2,3-epoxy-, (S)-;(2R)-2-(benzyloxymethyl)oxirane;R-Benzyl glycidyl ether;(R)-Benzyloxymethyloxirane;(R)- benzyl glycidyl ether;Benzyl((S)-glycidyl) ether;SCHEMBL715660;benzyl(R)-(+)-glycidyl ether;benzyl(R)-(-)-glycidyl ether;(-)-benzyl-(R)-glycidyl ether;BDBM36041;benzyl (R)-(+)-glycidyl ether;DTXSID10932782;(2R)-benzyl 2-epoxypropyl ether;CS-B1359;GEO-04308;AKOS015888105;AC-7034;AM81466;(R)-(-)-2-(Benzyloxymethyl)-oxirane;(R)-(-)-Glycidyl benzyl ether, 99%;NCGC00166044-01;AS-12082;LS-119621;B2238;EN300-74956;I10135;Oxirane, ((phenylmethoxy)methyl)-, (R)- (9CI);Q-101291;Z1171222157;2-Benzyloxymethyl-oxirane

Chemical Property of (R)-(-)-Benzyl glycidyl ether

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.0303mmHg at 25°C
• Melting Point: 88-93°C
• Refractive Index: n20/D 1.517(lit.)
• Boiling Point: 252.7 °C at 760 mmHg
• Flash Point: 100.9 °C
• PSA: 21.76000
• Density: 1.102 g/cm³
• LogP: 1.60200
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 130

Purity/Quality:

98% ^*data from raw suppliers

(R)-(?)-Glycidyl benzyl ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)COCC2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](O1)COCC2=CC=CC=C2
• 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.

Technology Process of (R)-(-)-Benzyl glycidyl ether

There total 82 articles about (R)-(-)-Benzyl glycidyl ether 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: 100.0%

benzyl bromide (100-39-0) + (R)-oxiranemethanol (57044-25-4) → (S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.200800154

Reference yield: 97.0%

(R)-3-(benzyloxy)-2-hydroxypropyl 4-methylbenzene sulfonate (23214-66-6) → (S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9)

Guidance literature:

With potassium carbonate; In methanol; 1.) -10 deg C, 2 h; 2.) r.t., 2 h;

DOI:10.1016/S0040-4039(00)99116-0

Reference yield: 95.0%

(S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + benzyl alcohol (100-51-6,185532-71-2) → (S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9)

Guidance literature:

(S)-epichlorohydrin; With tetrabutylammomium bromide; sodium hydroxide; In water; at 20 ℃;

benzyl alcohol; In water; at 20 ℃; regioselective reaction;

DOI:10.1039/c2ob26329g

upstream raw materials:

(S)-Benzyl-(3-benzoyloxy-2-p-tosyloxy-propyl)-ether

benzyl allyl ether

(R)-3-benzyloxy-1,2-propanediol

(R)-3-(benzyloxy)-2-hydroxypropyl 4-methylbenzene sulfonate

Downstream raw materials:

(R)-1-benzyloxy-2-hydroxyhexadecane

(R)-1-(Benzyloxy)-4-tetracosyn-2-ol

(R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-4-hydroxy-pentanenitrile

(2S)-1-(Phenylmethoxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentanol

Refernces

• 1、 Baig, Mirza Hamed A.,Baskaran, Subramanian,Banerjee, Sharmila,Trivedi, Girish K.. "Stereoselective total synthesis of (2R,2′S,3Z)-1-O-(2-methoxyhexadecenyl) glycerol and (2R,2′S)-1-(2′-methoxyhexadecyl)glycerol-potential antitumour compounds from Shark liver oil". . p. 4723 - 4732. Retrieved 1995.
• 2、 Hansen, Trond Vidar,Waagen, Viggo,Partali, Vassilia,Anthonsen, Henrik W.,Anthonsen, Thorleif. "Co-Solvent Enhancement of Enantioselectivity in Lipase-Catalysed Hydrolysis of Racemic Esters. A Process for Production of Homochiral C-3 Building Blocks using Lipase B from Candida antarctica". . p. 499 - 504. Retrieved 1995.
• 3、 Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu. "Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones". supporting information. p. 18039 - 18042. Retrieved 2021/11/16.
• 4、 González-Gil, Inés,Zian, Debora,Vázquez-Villa, Henar,Hernández-Torres, Gloria,Martínez, R. Fernando,Khiar-Fernández, Nora,Rivera, Richard,Kihara, Yasuyuki,Devesa, Isabel,Mathivanan, Sakthikumar,Del Valle, Cristina Rosell,Zambrana-Infantes, Emma,Puigdomenech, María,Cincilla, Giovanni,Sanchez-Martinez, Melchor,Rodríguez De Fonseca, Fernando,Ferrer-Montiel, Antonio V.,Chun, Jerold,López-Vales, Rubén,López-Rodríguez, María L.,Ortega-Gutiérrez, Silvia. "A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration". supporting information. p. 2372 - 2390. Retrieved 2020/01/02.