Category: 4972-31-0

Crich, David published the artcileIs Donor-Acceptor Hydrogen Bonding Necessary for 4,6-O-Benzylidene-directed β-Mannopyranosylation? Stereoselective Synthesis of β-C-Mannopyranosides and α-C-Glucopyranosides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Organic Letters (2008), 10(21), 4731-4734, database is CAplus and MEDLINE.

2,3-Di-O-benzyl-4,6-O-benzylidene-thiohexopyranosides, on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose series the β-isomers are formed selectively whereas the glucose series provides the α-anomers. This selectivity pattern parallels that of O-glycoside formation and eliminates the need to consider donor-acceptor hydrogen bonding in the formation of the O-glycosides.

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 C11H15NOS, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Matsui, Ryosuke published the artcileConvergent Total Synthesis of (+)-TMC-151C by a Vinylogous Mukaiyama Aldol Reaction and Ring-Closing Metathesis, Formula: C11H15NOS, the publication is Angewandte Chemie, International Edition (2011), 50(3), 680-683, S680/1-S680/66, database is CAplus and MEDLINE.

Total synthesis of (+)-TMC-151C by a highly convergent synthetic route, is reported. Characteristic features of the present synthesis include the construction of the C₁-C₅ and C9-C₁₃ units by vinylogous Mukaiyama aldol reactions and the use of a silicon-tethered diene for the stereoselective formation of the C₆-C₇ double bond by our recently developed E-selective ring-closing metathesis reaction to give an eight-membered ring. This synthetic strategy should provide efficient access to a range of related naturally occurring polyketides containing pent-2-ene-1,5-diol units.

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 C11H15NOS, Formula: C11H15NOS.

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

Goto, Kenta published the artcileThe Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture, COA of Formula: C11H15NOS, the publication is Chemistry – A European Journal (2016), 22(24), 8323-8331, database is CAplus and MEDLINE.

The total synthesis of ganglioside GP3, which is found in the starfish Asterina pectinifera, has been accomplished through stereoselective and effective glycosylation reactions. The sialic acid embedded octasaccharide moiety of the target compound was constructed by [4+4] convergent coupling. A tetrasaccharyl donor and acceptor that contained internal sialic acid residues were synthesized with an orthogonally protected N-Troc sialic acid donor as the key common synthetic unit, and they underwent highly stereoselective glycosidation. The resulting sialosides were subsequently transformed into reactive glycosyl acceptors. [4+4] coupling furnished the octasaccharide framework in 91 % yield as a single stereoisomer. Final conjugation of the octasaccharyl donor and glucosyl ceramide acceptor produced the protected target compound in high yield, which underwent global deprotection to successfully deliver ganglioside GP3.

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, COA of Formula: C11H15NOS.

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

Mukherjee, Chinmoy published the artcileSynthesis and Immunological Screening of β-Linked Mono- and Divalent Mannosides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is European Journal of Organic Chemistry (2012), 2012(15), 2957-2968, database is CAplus.

Three different β-linked divalent mannosides, along with their corresponding monovalent counterparts, have been designed and chem. synthesized by coupling the corresponding propargyl (propargyl alc. in the case of the monovalent compounds) and 2-azidoethyl glycosides by using an efficient click chem. protocol. Crich’s β-mannosylation methodol. was applied to the construction of the β-mannosidic linkages. All the glycosylation reactions gave moderate-to-good yields with high selectivities. A competitive inhibition ELISA was performed to determine the inhibition, by the synthesized mannosides, of specific human IgG binding to low-mol.-weight Candida albicans mannan; moderate inhibition capacity was observed for some of the compounds

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, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Izzo, Flavia published the artcileA New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides, Application of 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2017), 23(60), 15189-15193, database is CAplus and MEDLINE.

Unprotected tertiary sulfonimidamides RS(O)(=NH)X (R = Ph, (CH₃)₂CH, cyclohexyl, 2-pyridyl, etc.; X = 1-piperidinyl, N(CH₃)₂, (CH₃)N(CH₂)₂OCH₃, etc.) have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides RS(O)X through NH transfer. The reaction is mediated by com. available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups is tolerated and initial results indicate that the NH transfer is stereospecific. A small mol. X-ray anal. of 1-(S-phenylsulfonimidoyl)piperidine and its behavior in selected in vitro assays in comparison to the matched 1-benzenesulfonyl-piperidine are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

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, Application of 1-(Phenylsulfinyl)piperidine.

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

Chassagne, Pierre published the artcileConcise synthesis of di- and trisaccharides related to the O-antigens from Shigella flexneri serotypes 6 and 6a, based on late stage mono-O-acetylation and/or site-selective oxidation, Synthetic Route of 4972-31-0, the publication is Tetrahedron (2013), 69(48), 10337-10350, database is CAplus.

Shigella flexneri serotypes 6 and 6a are closely related bacteria causing Shigellosis in human. Their O-antigens are {(→4)-β-D-GalpA-(1→3)-β-D-GalpNAc-(1→2)-[3Ac/4Ac]-α-L-Rhap-(1→2)-α-L-Rhap-(1→)}_n acidic polysaccharides ({AB_AcCD}n), which only differ in the degree of O-acetylation. A concise synthesis of two disaccharides and four trisaccharides, representing portions and/or analogs of the O-antigens, is described. A protected intermediate compatible with late stage O-acetylation, and/or galactosyl to galacturonic acid conversion, was designed and assembled from trichloroacetimidate and thioglycoside donors tuned for high yielding glycosylation and excellent stereocontrol. The galacturonic moiety was efficiently introduced from galactose using a TEMPO/NaOCl/NaClO₂-based oxidation protocol optimized for full compatibility with sensitive moieties, such as allyl ethers and acetates. BC and ABC oligosaccharides are also portions of the O-antigen from Escherichia coli O147, which causes diarrhea in pigs.

Tetrahedron 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

Crich, David published the artcile1-benzenesulfinyl piperidine (BSP)/triflic anhydride. An effective combination for the hydrolysis of dithioacetals, Related Products of piperidines, the publication is Synlett (2003), 1257-1258, database is CAplus.

The combination of 1-benzenesulfinyl piperidine and triflic anhydride, in conjunction with an aqueous workup, hydrolyzes a broad range of dithioacetals to the corresponding carbonyl compounds under very mild, non-oxidative conditions.

Synlett 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 Synthesis of the β-L-Rhamnopyranosides, Name: 1-(Phenylsulfinyl)piperidine, the publication is Organic Letters (2003), 5(5), 781-784, database is CAplus and MEDLINE.

The direct formation of β-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.

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 C11H15NOS, Name: 1-(Phenylsulfinyl)piperidine.

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

Crich, David published the artcileOn the Use of 3,5-O-Benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method, Category: piperidines, the publication is Journal of Organic Chemistry (2007), 72(5), 1553-1565, database is CAplus and MEDLINE.

A 2-O-benzyl-3,5-O-benzylidene-α-D-thioarabinofuranoside was obtained by reaction of the corresponding diol with α,α-dibromotoluene under basic conditions. On activation with 1-benzenesulfinyl piperidine, or di-Ph sulfoxide, and trifluoromethanesulfonic anhydride in dichloromethane at -55 °C, reaction with glycosyl acceptors affords anomeric mixtures with little or no selectivity. The analogous 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-D-thioarabinofuranoside also showed no significant selectivity under the 1-benzenesulfinyl piperidine or di-Ph sulfoxide conditions. With N-iodosuccinimide and silver trifluoromethanesulfonate the silylene acetal showed moderate to high β-selectivity, independent of the configuration of the starting thioglycoside. High β-selectivity was also obtained with a 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-arabinofuranosyl sulfoxide donor on activation with trifluoromethanesulfonic anhydride. The high β-selectivities obtained by the N-iodosuccinimide/silver trifluoromethanesulfonate and sulfoxide methods are consistent with a common intermediate, most likely to be the oxacarbenium ion. The poor selectivity observed on activation of the thioglycosides with the 1-benzenesulfinyl piperidine, or di-Ph sulfoxide, and trifluoromethanesulfonic anhydride methods appears to be the result of the formation of a complex mixture of glycosyl donors, as determined by low-temperature NMR work.

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

Crich, David published the artcileOn the nitrile effect in L-rhamnopyranosylation, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Carbohydrate Research (2006), 341(10), 1467-1475, database is CAplus and MEDLINE.

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the β-selectivity of a number of L-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated.

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, Safety of 1-(Phenylsulfinyl)piperidine.

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