(S)-(+)-Benzyl glycidyl ether

Base Information

• Chemical Name: (S)-(+)-Benzyl glycidyl ether
• CAS No.: 16495-13-9
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• Hs Code.: 29109000
• DSSTox Substance ID: DTXSID20167826
• Nikkaji Number: J82.509C
• Wikidata: Q72441195
• Mol file: 16495-13-9.mol

Synonyms:Oxirane,[(phenylmethoxy)methyl]-, (2S)- (9CI);Oxirane, [(phenylmethoxy)methyl]-, (S)-;Propane, 1-(benzyloxy)-2,3-epoxy-, (S)- (8CI);(+)-2-(Benzyloxymethyl)oxirane;(+)-Glycidyl benzyl ether;(2S)-2-[(Benzyloxy)methyl]oxirane;(S)-(Benzyloxymethyl)oxirane;(S)-2-(Benzyloxymethyl)oxirane;(S)-Glycidyl benzyl ether;Benzyl(S)-glycidyl ether;

Chemical Property of (S)-(+)-Benzyl glycidyl ether

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Refractive Index: n20/D 1.517
• 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
• Solubility.: Chloroform, Ethanol
• 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:

99% ^*data from raw suppliers

(S)-(+)-BenzylGlycidylEther ^*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: (S)-(+)-Benzyl Glycidyl Ether is used as a reactant in the synthesis of (+)-Discodermolide. (S)-(+)-Glycidyl benzyl ether may be employed for the total asymmetric synthesis of (+)-gigantecin.

Technology Process of (S)-(+)-Benzyl glycidyl ether

There total 44 articles about (S)-(+)-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:

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

(3S,5S)-5-Benzyloxymethyl-3-methyl-dihydro-furan-2-one

(3R,5S)-5-Benzyloxymethyl-3-methyl-dihydro-furan-2-one

(2R)-(-)-1-N-(trifluoroacetyl)-3-(phenylmethoxy)propan-2-ol

Refernces

• 1、 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.
• 2、 Li, Chuang,Kan, Ting-Ting,Hu, Die,Wang, Ting-Ting,Su, Yong-Jun,Zhang, Chen,Cheng, Jian-Qing,Wu, Min-Chen. "Improving the activity and enantioselectivity of PvEH1, a Phaseolus vulgaris epoxide hydrolase, for o-methylphenyl glycidyl ether by multiple site-directed mutagenesis on the basis of rational design". . . Retrieved 2019/08/01.