Category: 4972-31-0

Bai, Yu published the artcileSynthesis of n-octyl 2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1â†?)-3-amino-3-deoxy-β-D-galactopyranoside, an analog of the H-disaccharide antigen, Quality Control of 4972-31-0, the publication is Carbohydrate Research (2006), 341(10), 1702-1707, database is CAplus and MEDLINE.

The synthesis of an analog of the H-disaccharide antigen I, in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of I was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide I is of interest in studies directed towards understanding the mol. basis of substrate recognition by the blood group A and B glycosyltransferases.

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

Codee, Jeroen D. C. published the artcilePh₂SO/Tf₂O: a Powerful Promotor System in Chemoselective Glycosylations Using Thio Glycosides, Synthetic Route of 4972-31-0, the publication is Organic Letters (2003), 5(9), 1519-1522, database is CAplus and MEDLINE.

Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed.

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, Synthetic Route of 4972-31-0.

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

Kice, John L. published the artcileReactivity of nucleophiles toward and the site of nucleophilic attack on phenyl benzenethiolsulfinate, Formula: C11H15NOS, the publication is Journal of Organic Chemistry (1979), 44(12), 1918-23, database is CAplus.

The reactivity of 12 common nucleophiles toward PhS(O)SPh (I) was measured and compared with their reactivity toward PhSO₂SPh (II) under the same conditions. Whether nucleophilic attack on I occurs preferentially on the di- or tetravalent S was determined for those nucleophiles where the nature and stability of the substitution make this possible. Most nucleophiles attack the sulfenyl rather than the sulfinyl S. Besides being the 1 type of nucleophile that prefers to attack the sulfinyl S I, oxyanions (e.g., MeO^–, OH) are also the 1 type of nucleophile that reacts with I at a rate closely comparable to that with II. All other types of nucleophiles are much less reactive toward I than toward II, the magnitude of the effect ranging from a factor of 20-40 for CN^–, SO₃^2- and PhS^– to a factor of 400-700 for common amines. The very low reactivity of amines and N^–₃ ion toward I may result from attack of the nucleophile not being the rate-determining step in these particular substitutions.

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, Formula: C11H15NOS.

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

Crich, David published the artcileThe 4-(tert-Butyldiphenylsiloxy)-3-fluorobenzyl Group: A New Alcohol Protecting Group, Fully Orthogonal with the p-Methoxybenzyl Group and Removable under Desilylation Conditions, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2009), 74(6), 2486-2493, database is CAplus and MEDLINE.

A new benzyl ether-type protecting group for alcs., the 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, is introduced. The protecting group is introduced by means of the readily prepared benzyl bromide and is cleaved with tetrabutylammonium fluoride in DMF under microwave irradiation The fluoride substituent provides stability to oxidizing conditions, such that the new protecting group is fully compatible with the removal of p-methoxybenzyl ethers with DDQ. Applications of the new protecting group in the direct stereocontrolled synthesis of β-mannopyranosides are presented.

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

Crich, David published the artcileSynthesis of the Salmonella Type E₁ Core Trisaccharide as a Probe for the Generality of 1-(Benzenesulfinyl)piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides, Name: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2002), 67(14), 4640-4646, database is CAplus and MEDLINE.

A synthesis of a chromogenic glycoside of the Salmonella anatum group E₁ core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-α-L-rhamnopyranosyl thioglycosides are found to be highly α-selective rhamnosyl donors under these conditions.

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, Name: 1-(Phenylsulfinyl)piperidine.

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

Morelli, Laura published the artcile2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study, Computed Properties of 4972-31-0, the publication is Carbohydrate Research (2021), 108421, database is CAplus and MEDLINE.

The role of the cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose, promoted by BSP/Tf₂O via α-triflate intermediates, has been investigated through a combined computational and exptl. approach. DFT calculations were used to locate the transition states leading to the α or β anomers. These data indicate the preferential formation of the β-adduct with mannosyl donors either equipped with the 4,6-O-benzylidene protection or without it. The synthetic results confirmed this preference, showing in both cases an α/β selectivity of 4:6. This highlights a role for the 2,3-N,O-carbamate in sharp contrast with what described in the case of 2,3-O-carbonate mannosyl donors.

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, Computed Properties of 4972-31-0.

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

Wudl, Fred published the artcileAsymmetric synthesis of chiral sulfoxides. II. Intramolecular oxygen to nitrogen sulfinyl migration, Synthetic Route of 4972-31-0, the publication is Journal of the American Chemical Society (1973), 95(19), 6349-58, database is CAplus.

The conversion of a 1,2,3-oxathiazolidine 2-oxide (I), derived from l-ephedrine, to Me aryl sulfoxides via sulfinamides (II; R = Me, Ph, MeC6H4) was studied in detail. The stereochem. of sulfinyl transfer in an O-sulfinylated ethanolamine (III) was investigated. This rearrangement proceeds via two competitive paths: intramol. and intermol. The intramol. path yields II with retention of configuration at S.

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 C7H8O3, Synthetic Route of 4972-31-0.

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

Baek, Ju Yuel published the artcileβ-Directing Effect of Electron-Withdrawing Groups at O-3, O-4, and O-6 Positions and α-Directing Effect by Remote Participation of 3-O-Acyl and 6-O-Acetyl Groups of Donors in Mannopyranosylations, Computed Properties of 4972-31-0, the publication is Journal of the American Chemical Society (2009), 131(48), 17705-17713, database is CAplus and MEDLINE.

Mannosylations of various acceptors with donors possessing an electron-withdrawing o-trifluoromethylbenzenesulfonyl, benzylsulfonyl, p-nitrobenzoyl, benzoyl, or acetyl group at O-3, O-4, or O-6 positions were found to be β-selective except when donors had 3-O-acyl and 6-O-acetyl groups, which afforded α-mannosides as major products. The α-directing effect of 3-O-acyl and 6-O-acetyl groups was attributed to their remote participation, and the isolation of a stable bicyclic trichlorooxazine ring resulting from the intramol. trapping of the anomeric oxocarbenium ion by 3-O-trichloroacetimidoyl group provided evidence for this remote participation. The triflate anion, counteranion of the mannosyl oxocarbenium ion, was essential for the β-selectivity, and covalent α-mannosyl triflates with an electron-withdrawing group at O-3, O-4, or O-6 were detected by low-temperature NMR. The strongly electron-withdrawing sulfonyl groups, which exhibited a higher β-directing effect in the mannosylation, made the α-mannosyl triflates more stable than the weakly electron-withdrawing acyl groups. We therefore proposed the mechanism for the β-mannosylation and the origin of the β-directing effect: the electron-withdrawing groups would stabilize the α-mannosyl triflate intermediate, and the subsequent reaction of the α-triflate (or its contact ion pair) with the acceptor would afford the β-mannoside. The β-selective mannosylation of a sterically demanding acceptor was achieved by employing a donor possessing two strongly electron-withdrawing benzylsulfonyl groups at O-4 and O-6 positions.

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, Computed Properties of 4972-31-0.

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

Lu, Yin-Jen published the artcile2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2018), 83(7), 3688-3701, database is CAplus and MEDLINE.

This study examines the utility of the N-benzylcarbamoyl (BnCar) protecting group in glycosylation reactions of the parent O-2 protected carbohydrate donor. It was found that the BnCar group imparted exclusively β-selectivity with primary and secondary alcs. A mechanistic study revealed the activated intermediate to be the glycosyl triflate in a skew conformation, which results in β-selective glycosylation via an S_N2-like pathway. The BnCar group can be readily cleaved using tetrabutylammonium nitrite, without affecting ester and ether protecting groups. Taken together, these results show BnCar to be useful for the synthesis of complex oligosaccharides, an undertaking that requires delicate chem. differentiation of various protecting groups.

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

Wang, Shuai published the artcileGlycosylation of ‘basic’ alcohols: methyl 6-(hydroxymethyl)picolinate as a case study, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Carbohydrate Research (2013), 35-46, database is CAplus and MEDLINE.

Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving Me 6-(hydroxymethyl)picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides.

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 C13H10O3, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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