Category: 4972-31-0

Wang, Liming published the artcileReagent Controlled Stereoselective Synthesis of α-Glucans, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (2018), 140(13), 4632-4638, database is CAplus and MEDLINE.

The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of a glycosylation reaction can vary greatly when switching form one glycosyl donor-acceptor pair to another. We here report a strategy to install cis-glucosidic linkages in a fully stereoselective fashion that is under direct control of the reagents used to activate a single type of donor building block. The activating reagents are tuned to the intrinsic reactivity of the acceptor alc. to match the reactivity of the glycosylation agent with the reactivity of the incoming nucleophile. A protecting group strategy is introduced that is based on the sole use of benzyl-ether type protecting groups to circumvent changes in reactivity as a result of the protecting groups. For the stereoselective construction of the α-glucosyl linkages to a secondary alc., a per-benzylated glusosyl imidate donor is activated with a combination of trimethylsilyltriflate and DMF, while activation of the same imidate donor with trimethylsilyl iodide in the presence of triphenylphosphine oxide allows for the stereoselective cis-glucosylation of primary alcs. The effectiveness of the strategy is illustrated in the modular synthesis of a Mycobacterium tuberculosis nonasaccharide, composed of an α-(1-4)-oligoglucose backbone bearing different α-glucosyl branches.

Journal of the American Chemical Society published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C18H22BNO7, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Furukawa, Mitsuru published the artcileNovel one-step preparation of sulfinic acid derivatives from sulfinic acid, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemical & Pharmaceutical Bulletin (1980), 28(1), 134-41, database is CAplus.

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 EtO₂CN:NCO₂Et-PPh₃. Ammonolysis of sulfinate esters also gave sulfinamides.

Chemical & Pharmaceutical Bulletin published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Bindschadler, Pascal published the artcileSynthesis of a potential 10E4 tetrasaccharide antigen involved in scrapie pathogenesis, COA of Formula: C11H15NOS, the publication is Helvetica Chimica Acta (2006), 89(11), 2591-2610, database is CAplus.

To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2+2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biol. role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using Traut’s reagent. During the course of the synthesis, the N,N-diacetyl protecting group proved surprisingly labile to radical and acidic conditions.

Helvetica Chimica Acta published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, COA of Formula: C11H15NOS.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Campbell, A. F. published the artcileThe separation of m-and p-cresols from coal-tar crude carbolic acid, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1922), 732-7, database is CAplus.

The fractions obtained by the distillation of the crude product consist principally of (1) PHOH, (2) o-cresol, (3) m- and p-cresols and (4) xylenols and other complex phenols. Fractionation of (3) gives a PhOH-free product containing 59-60% m-cresol. The sulfonation of this with 96%, H₂SO₄ at 40 for 6 hrs., and subsequent treatment with H₂O gives an extract (A) of non-sulfonated cresols and an aqueous solution (B) of monosulfonates containing 78-80% of the m-compound B is converted into the NH₄ salts through the Ba salts and on fractional crystallization yields a product containing 98-100% m-cresol. The further sulfonation of A with 96% H₂SO₄ gives a non-sulfonated product (C) containing about 80% p-cresol and a sulfonated product (D) containing about 58% m-cresol, which is further sulfonated for obtaining the m-compound C may be treated so that a product containing 89% p-cresol is obtained.

Journal of Industrial and Engineering Chemistry (Washington, D. C.) published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Zhang, Xiaheng published the artcileTotal synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects, Application of 1-(Phenylsulfinyl)piperidine, the publication is Nature Communications (2015), 5879, database is CAplus and MEDLINE.

Periploside A is a pregnane hexasaccharide identified from the Chinese medicinal plant Periploca sepium, which features a unique seven-membered formyl acetal bridged orthoester (FABO) motif and potent immunosuppressive activities. Here, we show the synthesis of this mol. in a total of 76 steps with the longest linear sequence of 29 steps and 9.2% overall yield. The FABO motif is constructed via a combination of Sinay’s and Crich’s protocol for the formation of orthoester and acetal glycosides, resp. The 2-deoxy-β-glycosidic linkages are assembled stereoselectively with judicious choice of the glycosylation methods. The epimer at the spiro-quaternary carbon in the FABO motif has also been elaborated in a stereo-controlled manner. This epimer, as well as the synthetic analogs bearing the FABO motif, retain largely the inhibitory activities of periploside A against the proliferation of T-lymphocyte, indicating the importance of the chem. connection of the FABO motif to their immunosuppressive activity.

Nature Communications published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C8H19NO2, Application of 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Chen, Jianfang published the artcileSynthesis of a tetrasaccharide substrate of heparanase, Quality Control of 4972-31-0, the publication is Carbohydrate Research (2008), 343(17), 2853-2862, database is CAplus and MEDLINE.

A tetrasaccharide, corresponding to the heparan sulfate heparanase substrate, namely β-D-GlcA(2S)-(1â†?)-α-D-GlcN(NS,6S)-(1â†?)-β-D-GlcA-(1â†?)-α-D-GlcN(NS,6S)-OMe, was synthesized in a convergent manner via coupling of a pair of the disaccharide building blocks as a key step.

Carbohydrate Research published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Quality Control of 4972-31-0.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Dai, Qiang published the artcileDirect Synthesis of Sulfinamides by the Copper-Catalyzed Electrophilic Amidation of Sulfenate Anions, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Advanced Synthesis & Catalysis (2018), 360(6), 1123-1127, database is CAplus.

A method for the construction of sulfinamides, e.g., I, 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.

Advanced Synthesis & Catalysis published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Yamago, Shigeru published the artcileIterative glycosylation of 2-deoxy-2-aminothioglycosides and its application to the combinatorial synthesis of linear oligo-glucosamines, Application of 1-(Phenylsulfinyl)piperidine, the publication is Angewandte Chemie, International Edition (2004), 43(16), 2145-2148, database is CAplus and MEDLINE.

Highly efficient coupling is observed with thioglycosides, which act both as glycosyl donors and acceptors. The iteration of the glycoside-coupling reaction under the same conditions allows the rapid assembly of a library of linear oligo-glucosamines (Phth = phthaloyl).

Angewandte Chemie, International Edition published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C3H5BN2O2, Application of 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Crich, David published the artcileBenzylidene Acetal Fragmentation Route to 6-Deoxy Sugars: Direct Reductive Cleavage in the Presence of Ether Protecting Groups, Permitting the Efficient, Highly Stereocontrolled Synthesis of β-D-Rhamnosides from D-Mannosyl Glycosyl Donors. Total Synthesis of α-D-Gal-(1â†?)-α-D-Rha-(1â†?)-β-D-Rha-(1â†?)-β-D-Glu-OMe, the Repeating Unit of the Antigenic Lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652, Related Products of piperidines, the publication is Journal of the American Chemical Society (2004), 126(26), 8232-8236, database is CAplus and MEDLINE.

An approach to the stereocontrolled synthesis of β-D-rhamnopyranosides is described in which 2,3-O-benzyl or related 4,6-O-[α-(2-(2-iodophenyl)ethylthiocarbonyl)benzylidene]-mannosyl thioglycosides are first used to introduce the β-D-mannopyranoside linkage in high yield and stereoselectivity. Following glycosylation, treatment with tributyltin hydride in toluene at reflux brings about reductive radical fragmentation directly to the 6-deoxy sugar in high yield. A variation of these donors bearing a carboxylated donor on O3 is a highly α-selective mannosyl and, after radical fragmentation, α-D-rhamnosyl donor. Using this stereoselective glycosylation/radical-fragmentation approach, a concise synthesis of the title tetrasaccharide is realized in which both the β-D– and α-D-rhamnopyranosyl units are obtained in a single step by a double radical fragmentation of the modified benzylidene acetals.

Journal of the American Chemical Society published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Crich, David published the artcileDirect Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides: Importance of the Nitrogen Protecting Group on Stereoselectivity, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2007), 72(14), 5183-5192, database is CAplus and MEDLINE.

The highly stereocontrolled synthesis of the 3-amino-3-deoxy-β-mannopyranosides is achieved by means of thioglycoside donors protected with a 4,6-O-benzylidene or alkylidene acetal and a benzylidene imine group. Among the various nitrogen protecting groups investigated only the Schiff’s base was found to give high β-selectivity. N-Phthalimido and N-acetamido protected donors were found to be highly α-selective, whereas 3-azido-3-deoxy glycosyl donors gave intermediate selectivity. The reasons for the protecting group dependency are discussed in terms of the change in the O2-C₂-C₃-N3 torsional interaction on conversion of the covalent glycosyl triflates to the transient oxa-carbenium ions.

Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem