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

Base Information

• Chemical Name: (S)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 58879-34-8
• Molecular Formula: C12H14O5S
• Molecular Weight: 270.306
• Hs Code.: 2932190090
• European Community (EC) Number: 623-559-8
• DSSTox Substance ID: DTXSID60974374
• Nikkaji Number: J3.618.392F
• Wikidata: Q76145943
• Mol file: 58879-34-8.mol

Synonyms:58879-34-8;(S)-(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate;(S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone;[(2S)-5-oxooxolan-2-yl]methyl 4-methylbenzenesulfonate;SCHEMBL506818;DTXSID60974374;MGAXYKDBRBNWKT-JTQLQIEISA-N;AKOS015840413;AKOS015913671;(S)--(+)-?-Tosyloxymethyl-?-butyrolactone;J3.618.392F;A832058;(S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)furanone;(S)-(+)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone;?(S)-(+)-Dihydro-5-(p-tolysulfonyioxymethyl)-2-(3H)-furanone;[(2S)-5-oxotetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate;p-Toluenesulfonic acid ((S)-5-oxotetrahydrofuran-2-yl)methyl ester;toluene-4-sulfonic acid (S)-5-oxo-tetrahydro-furan-2-ylmethyl ester;toluene4-sulfonic acid (S)-5-oxo-tetrahydro-furan-2-ylmethyl ester;(S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone, 98%

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.03E-09mmHg at 25°C
• Melting Point: 86-88 °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
• 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

(S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone 98% ^*data from reagent suppliers

Safty Information:

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

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

There total 22 articles about (S)-(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: 100.0%

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) + p-toluenesulfonyl chloride (98-59-9) → (S)-5-tosyloxypentan-4-olide (58879-34-8)

Guidance literature:

With pyridine; In chloroform; at 0 ℃; for 12h;

DOI:10.1021/ol051483k

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: 50.6%

[(2S)-tetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate (22415-60-7,34583-63-6,114114-90-8) → (S)-5-tosyloxypentan-4-olide (58879-34-8)

Guidance literature:

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

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

hypochlorous acid 4-methylbenzene sulfonic anhydride

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

p-toluenesulfonyl chloride

Downstream raw materials:

(R)-5-methyl-2-oxotetrahydrofuran

Toluene-4-sulfonic acid (2S,4S)-4-methyl-5-oxo-tetrahydro-furan-2-ylmethyl ester

((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-methyl benzenesulfonate

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

Refernces

• 1、 -. "METHOD FOR SYNTHESIZING A PRECURSOR OF A SINGLE DAIRY-LACTONE ISOMER". Paragraph 0045; 0065; 0066. . Retrieved 2018/03/25.
• 2、 Gelis, Coralie,Dumoulin, Audrey,Bekkaye, Mathieu,Neuville, Luc,Masson, Géraldine. "Chiral hypervalent iodine(III) catalyst promotes highly enantioselective sulfonyl-and phosphoryl-oxylactonizations". supporting information. p. 278 - 281. Retrieved 2017/11/27.