(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
• General Description: (R)-(-)-Benzyl glycidyl ether is a chiral epoxide derivative used as a key starting material in the enantioselective synthesis of complex natural products, such as (+)-aspergillide C. It serves as a versatile building block in organic synthesis, enabling the construction of stereochemically defined intermediates through reactions like olefination, epoxidation, and intramolecular oxy-Michael additions. Its (R)-configuration ensures the stereocontrol required for the diastereoselective formation of target molecules, as demonstrated in the synthesis of macrolides. The compound's reactivity and chiral integrity make it valuable for constructing epoxide-containing frameworks in multistep synthetic routes.

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:

(S)-1-Benzyloxy-3-(5-hydroxymethyl-furan-2-yl)-propan-2-ol

(R)-5-Benzyloxy-4-hydroxy-2-p-tolyl-pentanenitrile

(S)-1-Benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol

(S)-1-benzyloxy-4-decyn-2-ol

Refernces

Total synthesis of (+)-aspergillide C

10.1016/j.tetlet.2011.01.078

The research details the enantioselective total synthesis of (+)-aspergillide C, a 14-membered macrolide isolated from the marine-derived fungus Aspergillus ostianus. The key step in the synthesis process is a highly diastereoselective intramolecular oxy-Michael (IMOM) reaction involving a cis-epoxide and an E-enoate. The researchers used R-(-)-benzyl glycidyl ether as a starting material and employed a series of reactions including olefination, epoxidation, reduction, and the Horner–Wadsworth–Emmons reaction to synthesize the substrate for the IMOM reaction. The reaction conditions, such as the choice of base (KH, NaHMDS, LiHMDS) and the addition of water, were found to significantly affect the yield and diastereoselectivity of the anti-pyran product. The synthesized product was then converted to the natural product through a series of standard functional group transformations, including reduction, silylation, oxidation, and macrolactonization. The success of the synthesis was confirmed by comparing the spectroscopic properties of the synthesized (+)-aspergillide C with those reported for the natural product.