(R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 58879-33-7
• Molecular Formula: C12H14O5S
• Molecular Weight: 270.306
• Hs Code.: 2932190090
• European Community (EC) Number: 622-324-7
• DSSTox Substance ID: DTXSID10427365
• Nikkaji Number: J435.327G
• Wikidata: Q82240023
• Mol file: 58879-33-7.mol

Synonyms:58879-33-7;(R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate;[(2R)-5-oxooxolan-2-yl]methyl 4-methylbenzenesulfonate;R-(-)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone;(R)-(-)-Dihydro-5-(p-tolysulfonyioxymethyl)-2-(3H)-furanone;(R)-(-)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone;SCHEMBL898024;DTXSID10427365;MGAXYKDBRBNWKT-SNVBAGLBSA-N;2(3H)-Furanone, dihydro-5-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (R)-;AKOS015842556;(5R)-5alpha-(Tosyloxymethyl)oxolane-2-one;A869335;[(2R)-5-oxooxolan-2-yl]methyl 4-methylbenzene-1-sulfonate;(R)-(-)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone;(R)-(-)-Dihydro-5-(p-tolyl-sulfonyloxymethyl)-2(3H)-furanone;(R)-toluene-4-sulfonic acid 5-oxo-tetrahydrofuran-2-ylmethyl ester;Toluene-4-sulfonic acid (R)-5-oxo-tetrahydro-furan-2-ylmethyl ester;toluene4-sulfonic acid (R)-5-oxo-tetrahydro-furan-2-ylmethyl ester

Chemical Property of (R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 3.03E-09mmHg at 25°C
• Melting Point: 85-88 °C(lit.)
• Refractive Index: 1.542
• Boiling Point: 476.5 °C at 760 mmHg
• Flash Point: 242 °C
• PSA: 78.05000
• Density: 1.311 g/cm³
• LogP: 2.48670
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 270.05619472
• Heavy Atom Count: 18
• Complexity: 389

Purity/Quality:

99% ^*data from raw suppliers

(R)-(5-Oxotetrahydrofuran-2-yl)methyl4-methylbenzenesulfonate 95+% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CCC(=O)O2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CCC(=O)O2

Technology Process of (R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

There total 11 articles about (R)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 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: 90.0%

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + p-toluenesulfonyl chloride (98-59-9) → (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone (58879-33-7)

Guidance literature:

With pyridine;

DOI:10.1016/0040-4039(95)00083-O

Reference yield: 74.0%

pent-4-enoic acid (591-80-0) + toluene-4-sulfonic acid (104-15-4) → (S)-5-tosyloxypentan-4-olide (58879-34-8) + (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone (58879-33-7)

Guidance literature:

With (2R,2'R)-2,2'-([2-iodo-1,3-phenylene]bis(oxy))bis(N-mesitylpropanamide); 3-chloro-benzenecarboperoxoic acid; In diethyl ether; 2,2,2-trifluoroethanol; at -45 - 20 ℃; for 120h; Solvent; Temperature; Reagent/catalyst; Concentration; enantioselective reaction; Catalytic behavior;

DOI:10.1021/acs.orglett.6b03631

Reference yield: 53.8%

[(2R)-tetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate (22415-60-7,34583-63-6,114114-90-8) → (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone (58879-33-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; Ambient temperature;

upstream raw materials:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

p-toluenesulfonyl chloride

[(2R)-tetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate

L-glutamic acid

Downstream raw materials:

(2S)-2-methylbutane-1,4-diol

(5;R)-5-(4-{1-ethyl-1-[3'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic acid

(R)-5-(4-{1-ethyl-1-[3'-(1-hydroxy-2,2-dimethyl-propyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic acid

(R)-5-(4-{1-ethyl-1-[3'-(1-ethyl-1-hydroxypropyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic acid