58879-34-8

Basic information

• Product Name: (S)-(+)-DIHYDRO-5-(P-TOLYLSULFONYLOXYMETHYL)-2(3H)-FURANONE
• Synonyms: (S)-(+)-DIHYDRO-5-(P-TOLYLSULFONYLOXYMETHYL)-2(3H)-FURANONE;(S)-(+)-GAMMA-TOLUENESULFONYLMETHYL-GAMMA-BUTYROLACTONE;(S)-(+)-4,5-DIHYDRO-5[[(4-METHYLPHENYLSULFONYL)OXY]METHYL]-2(3H)-FURANONE;(S)-(+)-Toluenesulfonylmethyl)- -butyrolactone;S-(+)-GAMMA-TOSYLOXYMETHYL-GAMMA-BUTYRO- LACTONE;(s)-(+)-γ-tosyloxymethyl-γ-butyrolactone;(S)-(+)-g-Toluenesulfonylmethyl-g-butyrolactone.;(S)-(+)-GAMMA-TOLUENESULFONYLMETHYL-GAMMA-BUTYROLACTONE, 99+%
• CAS NO: 58879-34-8
• Molecular Formula: C₁₂H₁₄O₅S
• Molecular Weight: 270.3
• Mol File: 58879-34-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 383.42°C (rough estimate)
• Flash Point: 242 °C
• Appearance: white crystalline powder
• Density: 1.3900 (rough estimate)
• Vapor Pressure: 3.03E-09mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• BRN: 4701928
• CAS DataBase Reference: (S)-(+)-DIHYDRO-5-(P-TOLYLSULFONYLOXYMETHYL)-2(3H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-DIHYDRO-5-(P-TOLYLSULFONYLOXYMETHYL)-2(3H)-FURANONE(58879-34-8)
• EPA Substance Registry System: (S)-(+)-DIHYDRO-5-(P-TOLYLSULFONYLOXYMETHYL)-2(3H)-FURANONE(58879-34-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 58879-34-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C12H14O5S/c1-9-2-5-11(6-3-9)18(14,15)16-8-10-4-7-12(13)17-10/h2-3,5-6,10H,4,7-8H2,1H3/t10-/m0/s1

Upstream product

• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 821-09-0 n-Pent-4-enyl alcohol 
• 591-80-0 pent-4-enoic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 97-99-4 (S)-(tetrahydrofuran-2-yl)methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 74500-40-6 S-4,5-O-isopropylidene-4,5-dihydroxy-2-ethoxycarbonylpentanoic acid ethyl ester 
• 78185-08-7 (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one 
• 79580-68-0 di-O-acetyl-2-deoxy-D-threo-pentono-1,4-lactone 
• 79580-69-1 (S)-(+)-dihydro-5-(hydroxymethyl)-2(3H)-furanone acetate 
• 78138-87-1 potassium D-lyxonate 
• 78138-85-9 2-bromo-2-deoxy-D-xylono-1,4-lactone 
• 13095-47-1 (2R)-hydroxyglutaric acid 

Downstream Products

• 69830-91-7 (R)-4-dodecanolide 
• 58917-25-2 (R)-5-methyl-2-oxotetrahydrofuran 
• 107971-37-9 Toluene-4-sulfonic acid (2S,4S)-4-methyl-5-oxo-tetrahydro-furan-2-ylmethyl ester 
• 107971-37-9 ((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-methyl benzenesulfonate 
• 626-95-9 (2S)-2-methylbutane-1,4-diol 
• 101690-53-3 (S)-3-Oxiranyl-propionic acid benzyl ester 
• 62396-83-2 (S)-5-methyl-1-(toluene-4-sulfonyloxy)-hexane-2,5-diol 
• 22415-60-7 [(2S)-tetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate 
• 89872-57-1 (2S)-2,5-dihydroxy-1-tosyloxypentane 
• 471261-23-1 (2S)-toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-pentyl ester 
• 864182-70-7 (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide 
• 864270-18-8 (3R)-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]-1-{5-[(2E)-2-methyl-4-oxobut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}pent-4-enyl acetate 
• 864270-15-5 (3R)-1-{5-[(2E)-4-hydroxy-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate 
• 864270-19-9 (E)-4-{(R)-4-[(R)-1-Acetoxy-4-methyl-3-(5-methylene-2-phenyl-[1,3]dioxan-4-ylmethyl)-pent-4-enyl]-5-oxo-2,5-dihydro-furan-2-yl}-3-methyl-but-2-enoic acid 

Relevant articles and documents

A Reverse Approach to the Total Synthesis of Halichondrin B

A new strategy is described for the total synthesis of halichondrin B featuring reversal of the sequential construction of a number of its cyclic ethers from the classical approach by instead forming C-O bonds first followed by C-C bond formation. Employing the Nicholas reaction to generate linear ethers as precursors for the total synthesis of halichondrin B and other members of the halichondrin and eribulin families of compounds, this novel approach provides new opportunities for the development of improved syntheses of these complex and valuable compounds. In this Article, we report the syntheses of defined fragments I, MN, EFG, and A. Fragments I and MN were then coupled and elaborated to advanced intermediate IJKLMN, which was joined with fragment EFG to afford, after appropriate elaboration and macrolactonization, the more advanced polycyclic intermediate EFGHIJKLMN. Elaboration of the latter and coupling with fragment A followed by further functionalization completed the total synthesis of halichondrin B through a short and convergent pathway.

Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)?H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates

A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.

Chemo-enzymatic synthesis of chiral epoxides ethyl and methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable levoglucosenone: An access to enantiopure (S)-dairy lactone

Chiral epoxides-such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)-are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%-50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO.