Simple and Efficient Method for the Oxidation of Sulfides to Sulfoxides:  Application to the Preparation of Glycosyl Sulfoxides

Kakarla, Ramesh; Dulina, Richard; Hatzenbuhler, Nicole T.; Hui, Yan; Sofia, Michael J.

doi:10.1021/jo961478h

Cited by 65 publications

(37 citation statements)

References 33 publications

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“…6,158.2,151.6,149.5,131.2,128.7,128.6,127.6,122.1,111.8 (d,J 26.3 Hz),111.4 (d,J 9.5 Hz),105.3 (d,J 25.6 Hz),16.5. MS (EI,70 eV) m/z (relative intensity): 255 (100), 239 (64), 212 (92), 192 (12), 168 (30), 150 (6).…”

Section: -(Methylthio)-3-p-tolylbenzofuran (3c)mentioning

confidence: 99%

“…MS (EI,70 eV) m/z (relative intensity): 255 (100), 239 (64), 212 (92), 192 (12), 168 (30), 150 (6). -3-(4-methoxyphenyl)-2-(methylthio) 6,159.1,158.2,151.6,148.8,130.0,123.5,122.3,114.2,111.9 (d,J 24.8 Hz),111.4 (d,J 9.5 Hz),105.3 (d,J 24.8 Hz),55.3,16.7. MS (EI, 70 eV) m/z (relative intensity): 285 (100), 269 (73), 242 (49), 226 (14), 155.6 (17).…”

Section: -(Methylthio)-3-p-tolylbenzofuran (3c)mentioning

confidence: 99%

“…Among them, the use of potassium organotrifluoroborates, as the organoboron coupling partner, has some of these advantages are higher nucleophilicity, air-stability and ready access in comparison to boronic acids and boronic esters. 5 In addition, the presence of a sulfide group at the 2-position of benzo [b]furan is significant, since it could be easily oxidized to 2-sulfonylbenzofurans, 6 a class of compounds which has attracted tremendous interest from the pharmaceutical industry. During the course of our research program aiming at structure-activity relationship studies in order to evaluate the pharmacology activity of heterocycles, 7,8 we required the synthesis of benzofurans having an organochalcogen group at the 2-position and a substituted aromatic ring at the 3-position.…”

Section: Introductionmentioning

confidence: 99%

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Palladium catalyzed Suzuki cross-coupling of 3-iodo-2-(methylthio)-benzo[b]furan derivatives: synthesis of 3-aryl-2-(methylthio)benzo[b]furans

Gay¹,

Manarin²,

Brandão³

et al. 2010

J. Braz. Chem. Soc.

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Neste trabalho desenvolvemos um método seletivo e eficiente para a síntese de derivados de 3-aril-2-(tiometil)-benzo [b]furanos, via reação de acoplamento com ácidos borônicos, catalisada por paládio. As condições reacionais usadas foram brandas e compatíveis com ácidos borônicos contendo substituintes retiradores, doadores de elétrons ou neutros.A selective and efficient method for the synthesis of 3-aryl-2-(methylthio)benzo [b]furans derivatives by palladium catalyzed cross-coupling reaction with boronic acids has been developed. The reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron donating and neutral substituents.

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Section: -(Methylthio)-3-p-tolylbenzofuran (3c)mentioning

confidence: 99%

Section: -(Methylthio)-3-p-tolylbenzofuran (3c)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Palladium catalyzed Suzuki cross-coupling of 3-iodo-2-(methylthio)-benzo[b]furan derivatives: synthesis of 3-aryl-2-(methylthio)benzo[b]furans

Gay¹,

Manarin²,

Brandão³

et al. 2010

J. Braz. Chem. Soc.

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“…In a similar example, attempts to oxidize phenyl 2',3',4',6',2,3,6-hepta-O-acetyl-b-D-lactosyl thioglycoside to the sulfoxide 3 using a procedure which should prevent overoxidation to the sulfone 4 16 showed two compounds on the TLC plate (R f = 0.21 and R f = 0.11, petroleum ether/ EtOAc 1:1). Since the starting material contained traces of peracetylated lactose 5 (R f = 0.22), it was thought that the higher running compound was the peracetate.…”

Section: Product and Starting Materials With Identical R Fmentioning

confidence: 99%

Analysis of organic reactions by thin layer chromatography combined with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

Hilaire¹,

Cipolla²,

Tedebark³

et al. 1998

Rapid Commun. Mass Spectrom.

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The products of a wide variety of organic reactions were rapidly identified by their masses through a combination of thin layer chromatography (TLC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS). Crude mixtures of peptides and glycopeptides, complex carbohydrate reactions, and a classical organic reaction were analysed using the following standard protocol. The components of the reaction mixtures were first separated on the TLC plate, scraped off, extracted and analysed by MALDI-TOFMS. The technique used is easy and applicable to most organic reactions, becoming a very powerful technique in reaction optimization once composition and identity of TLC spots have been established by MS. Moreover, the TLC/MALDI-TOFMS method was used to identify low molecular weight compounds with masses within the matrix region (100-500 u), a goal which is normally difficult to achieve. We successfully detected low molecular weight compounds by suppression of the matrix peaks using a relatively low matrix:analyte ratio (15:1 or lower). Doping both matrix and analyte solutions with [Cs]+ ions resulted in suppression of both [Na]+ and [K]+ peaks, thus enhancing the spectral signals and making identification of low molecular weight compounds more facile.

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“…2e4 Typically they are produced by oxidation of the corresponding thioglycoside with meta-chloroperoxybenzoic acid (m-CPBA), although this reagent does suffer from limitations, including a propensity to cause over-oxidation to the sulfone, and also the formation of by-products that are difficult to remove. Other strategies that have been developed to circumvent the use of m-CPBA may also result in the formation of undesired by-products, 5 use equally difficult to work with reagents, 6e8 or complex procedures. 9 The development of a catalytic procedure that can effect the clean conversion of thioglycosides into the corresponding glycosyl sulfoxides would be advantageous, particularly if a low cost and easy to handle 'green' stoichiometric oxidant, such as hydrogen peroxide, 10e15 could be used.…”

Section: Introductionmentioning

confidence: 99%

Direct aqueous synthesis of non-protected glycosyl sulfoxides; weak inhibitory activity against glycosidases

Alexander

Watson

Fairbanks

2015

Carbohydrate Research

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Simple and Efficient Method for the Oxidation of Sulfides to Sulfoxides: Application to the Preparation of Glycosyl Sulfoxides

Cited by 65 publications

References 33 publications

Palladium catalyzed Suzuki cross-coupling of 3-iodo-2-(methylthio)-benzo[b]furan derivatives: synthesis of 3-aryl-2-(methylthio)benzo[b]furans

Palladium catalyzed Suzuki cross-coupling of 3-iodo-2-(methylthio)-benzo[b]furan derivatives: synthesis of 3-aryl-2-(methylthio)benzo[b]furans

Analysis of organic reactions by thin layer chromatography combined with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

Direct aqueous synthesis of non-protected glycosyl sulfoxides; weak inhibitory activity against glycosidases

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