Category: 4972-31-0

Litjens, Remy E. J. N. published the artcileSulfonium triflate mediated glycosidations of aryl 2-azido-2-deoxy-1-thio-D-mannosides, Category: piperidines, the publication is European Journal of Organic Chemistry (2005), 918-924, database is CAplus.

The effectiveness in terms of yield and stereoselectivity of (phenylsulfinyl)piperidine (BSP)/ trifluoromethanesulfonic anhydride (Tf₂O) and di-Ph sulfoxide (DPS)/ Tf₂O-mediated glycosidations of 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides is described. Application of the BSP/Tf₂O activator led to productive condensations using p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannoside as a donor, while the more powerful DPS/Tf₂O combination gave similar results using both p-methoxyphenyl and Ph 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides.

European 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, Category: piperidines.

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

Kumar, Chidambaram Ramesh published the artcileThe first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside, Name: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2011), 17(31), 8696-8703, S8696/1-S8696/29, database is CAplus and MEDLINE.

The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-β-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetra-yne by using various spectroscopic methods, but the chirality of the poly-yne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from com. available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol to give the desired β-glycoside and the construction of the glucosyl tetra-yne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne.

Chemistry – A European Journal 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, Name: 1-(Phenylsulfinyl)piperidine.

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

Nguyen, Son Hong published the artcileDirect O-glycosylation of resin bound thioglycosides, Product Details of C11H15NOS, the publication is Organic & Biomolecular Chemistry (2012), 10(12), 2373-2376, database is CAplus and MEDLINE.

The application to solid-phase glycoconjugate synthesis is described. The process allows for direct conjugation of resin bound glycans to complex aglycons during cleavage. Large excesses of either coupling partner are not required, and even very hindered alcs. serve as acceptors in the reaction.

Organic & Biomolecular 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, Product Details of C11H15NOS.

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

Son, Sang-Hyun published the artcilePre-activation of fully acetylated dodecyl thioglycosides with BSP-Tf₂O led to efficient glycosylation at low temperature, HPLC of Formula: 4972-31-0, the publication is Carbohydrate Research (2009), 344(3), 285-290, database is CAplus and MEDLINE.

Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf₂O) at -78 °C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le^a) trisaccharide, in good yields.

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 C8H11NO, HPLC of Formula: 4972-31-0.

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

Son, Sang-Hyun published the artcileStereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside, Application of 1-(Phenylsulfinyl)piperidine, the publication is Organic & Biomolecular Chemistry (2008), 6(8), 1441-1449, database is CAplus and MEDLINE.

Dodecyl thioglycosides (3, 4, 5) were prepared by conventional transformation of d-glucose and used as new glycosyl donors for a short-step synthesis of phytoalexin elicitor heptaglucoside. A gentio-tetraoside derivative (6) having three hydroxyl groups was synthesized by NIS-TfOH promoted glycosylate in more than 90% yield followed by selective removal of temporary protective groups. Undesired formation of α-glycosides at the introduction of β-(1→3)-branches into gentio-oligosaccharides was found to be suppressed by use of a thiophilic reagent system, BSP (1-benzenesulfinyl piperidine)-Tf₂O, giving the heptaglucoside in only four glycosylation steps.

Organic & Biomolecular 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 C28H18O4, Application of 1-(Phenylsulfinyl)piperidine.

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

Yamada, Takeshi published the artcileDialkyl-phosphates as stereo-directing protecting groups in oligosaccharide synthesis, Category: piperidines, the publication is Angewandte Chemie, International Edition (2006), 45(45), 7575-7578, database is CAplus and MEDLINE.

Double duty: A phosphoric ester at the C2 position in glycosyl donors directs the glycosylation to occur selectively at the anomeric carbon atom with complete 1,2-trans selectivity. Since the phosphoric ester can be removed to give the hydroxy function, this group serves as a stereo-directing protecting group in oligosaccharide synthesis.

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 C7H8BBrO3, Category: piperidines.

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

Crich, David published the artcileCyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride, HPLC of Formula: 4972-31-0, the publication is Heterocycles (2004), 827-830, database is CAplus.

The combination of a benzenesulfinamide, trifluoromethanesulfonic anhydride, and Huenig’s base brings about the cyclofunctionalization of unsaturated alcs., phenols, acids, and sulfonamides to give the corresponding α-phenylsulfanylmethyl cyclic ethers, lactones and sulfonamides, resp. In an unanticipated twist the products are isolated at the sulfur (II) oxidation state denoting an overall reduction in the oxidation state of the sulfur based electrophile in the course of the reaction.

Heterocycles 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, HPLC of Formula: 4972-31-0.

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

Wei, Juhong published the artciletert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds, COA of Formula: C11H15NOS, the publication is Organic Letters (2015), 17(21), 5396-5399, database is CAplus and MEDLINE.

Sulfoxides bearing a tert-Bu 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.

Organic Letters 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 C9H5ClO2, COA of Formula: C11H15NOS.

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

Crich, David published the artcile1-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, HPLC of Formula: 4972-31-0, the publication is Journal of the American Chemical Society (2001), 123(37), 9015-9020, database is CAplus and MEDLINE.

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 thio glycosides, via glycosyl triflates, in a matter of minutes at -60 °C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcs., in good yield and selectivity.

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, HPLC of Formula: 4972-31-0.

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

Crich, David published the artcileInfluence of the O3 Protecting Group on Stereoselectivity in the Preparation of C-Mannopyranosides with 4,6-O-Benzylidene Protected Donors, Synthetic Route of 4972-31-0, the publication is Journal of Organic Chemistry (2010), 75(24), 8383-8391, database is CAplus and MEDLINE.

α-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with di-Ph sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.

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, Synthetic Route of 4972-31-0.

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