4972-31-0

Usage

Uses

1-(Phenylsulfinyl)piperidine 97 is used as a reagent in the selective glycosylation of mannopyranols, which is crucial for the synthesis of complex carbohydrates and their derivatives. This selective glycosylation is essential in the development of new drugs and the study of carbohydrate-based interactions in biological systems.
Used in Pharmaceutical Industry:
1-(Phenylsulfinyl)piperidine 97 is used as a reagent for the preparation of aminoglycoside antibiotics, which are a class of antibiotics known for their broad-spectrum activity against both Gram-negative and Gram-positive bacteria. These antibiotics are widely used to treat various bacterial infections.
Used in Carbohydrate Chemistry:
1-(Phenylsulfinyl)piperidine 97 is used as a reagent for the design of enzyme stabilizers, which are essential in enhancing the stability and activity of enzymes in various industrial and research applications.
Used in Glycan Chemistry:
1-(Phenylsulfinyl)piperidine 97 is used as a reagent for the synthesis of a glycan array, which is a collection of diverse carbohydrates used for affinity studies with influenza hemagglutinins. These studies are vital for understanding the interactions between carbohydrates and proteins, which can lead to the development of new therapeutic strategies against viral infections.
Used in Oligosaccharide Synthesis:
1-(Phenylsulfinyl)piperidine 97 is used as a reagent for the preparation of orthogonal protecting groups, which are essential in the synthesis of highly branched oligosaccharides. These complex carbohydrates have potential applications in drug development, vaccine design, and the study of carbohydrate-based interactions in biological systems.
Used in Bacterial Polysaccharide Synthesis:
1-(Phenylsulfinyl)piperidine 97 is used as a reagent for the synthesis of tetrasaccharide repeating units related to E. Coli 78 O-antigenic polysaccharides. These polysaccharides are crucial for the development of vaccines and the study of bacterial pathogenesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 1931, 1984 DOI: 10.1021/jo00185a017Chemical and Pharmaceutical Bulletin, 28, p. 134, 1980 DOI: 10.1248/cpb.28.134

InChI:InChI=1/C11H15NOS/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8H,2,5-6,9-10H2

Upstream product

• 110-89-4 piperidine 
• 4972-29-6 benzenesulphinyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 98-09-9 benzenesulfonyl chloride 
• 882-33-7 diphenyldisulfane 
• 5542-49-4 piperidin-1-yl benzoate 
• 873-55-2 sodium benzenesulfonate 
• 931-59-9 benzenesulfenyl chloride 
• 62076-10-2 (tert-butylsulfinyl)benzene 

Downstream Products

• 110911-18-7 2-((phenylthio)methyl)tetrahydro-2H-pyran 
• 17414-08-3 2-<(phenylthio)methyl>tetrahydrofuran 
• 108078-64-4 5-[(phenylsulfanyl)methyl]dihydrofuran-2(3H)-2-one 
• 74455-32-6 2-((phenylthio)methyl)-2,3-dihydrobenzofuran 
• 894358-74-8 C₄₀H₄₀O₆S₂ 
• 1052273-95-6 C₄₀H₄₀O₆S₂ 

Relevant academic research and scientific papers

N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis

The pharmaceutically underexplored sulfoximine moiety has emerged as a potentially active pharmaceutical ingredient. We developed a scalable synthetic route to N-arylated sulfoximines from the respective "free" NH-sulfoximines and bromoarenes. Our strategy is based on a dual nickel photocatalytic approach, is applicable for a broad scope of substrates, and exhibits a highly functional group tolerance. In addition, we could demonstrate that other sulfoximidoyl derivatives like sulfonimidamides and sulfinamides proceed smoothly under the developed reaction conditions.

A Selectfluor-promoted oxidative reaction of disulfides and amines: access to sulfinamides

An unprecedented transition-metal-free oxidative reaction of disulfides and amines with Selectfluor as a mild oxidant under aerobic conditions was developed. This reaction was conducted under mild conditions and tolerated a wide range of coupling partners including disulfides and amines, affording the corresponding sulfinamide products in good chemical yields. Furthermore, this reaction could be used in gram-scale synthesis. This reaction enriches the research content of Selectfluor and provides a valuable vista for the convenient synthesis of sulfinamides.

Direct Synthesis of Sulfinamides by the Copper-Catalyzed Electrophilic Amidation of Sulfenate Anions

A method for the construction of sulfinamides via the copper-catalyzed electrophilic amination of sulfenate anions using N-benzoyloxyamines as the amination reagents. This procedure featured with the capture of in-situ generated sulfenate anions from β-sulfinyl esters under mild conditions, which provides an efficient strategy for the synthesis of diverse sulfinamides in moderate to good yields. (Figure presented.).

Tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds

Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.

Improved synthesis of 1-benzenesulfinyl piperidine and analogs for the activation of thioglycosides in conjunction with trifluoromethanesulfonic anhydride

An improved protocol for the large-scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-diethyl benzenesulfinamide function analogously to 1-benzenesulfinyl pip

Method of forming glycosidic bonds from thioglycosides using an N,N-dialkylsulfinamide

A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacc

1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages

The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf2O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matte

Selective Alkylation of β-Ketoester Enolates using O-Methyl Aminosulfoxonium salts; the First Example of C-alkylation using Sulfoxonium Salt Electrophiles

The alkylation of β-ketoester enolates with O-methyl aminosulfoxonium tetraphenylborate salts is reported; good to excellent selectivity for C- vs.O-alkylation is observed, and is found to be dependent on the nature of the β-ketoester, solvent, metal counterion and aminosulfoxonium salt.

Novel One-Step Preparation of Sulfinic Acid Derivatives from Sulfinic Acid

Convenient one-step syntheses of sulfinamides and sulfinate esters from sulfinic acids were achieved by using coupling reagents, such as 2-chloro-1-methylpyridinium iodide, γ-saccharine chloride, N,N'-dicyclohexylcarbodiimide, and diethyl azodicarboxylate and triphenylphosphine.Ammonolysis of sulfinate esters also give sulfinamides.Keyword- sulfinic acid; sulfinamide; sulfinate ester; sulfinyl-transfer reagent; coupling reaction; 2-chloro-1-methylpyridinium iodide; γ-saccharine chloride; N,N'-dicyclohexylcarbodiimide; diethyl azodicarboxylate; triphenylphosphine