Tag: M.W=200-250

Crich, David published the artcileDoes Neighboring Group Participation by Non-Vicinal Esters Play a Role in Glycosylation Reactions? Effective Probes for the Detection of Bridging Intermediates, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2008), 73(22), 8942-8953, database is CAplus and MEDLINE.

Neighboring group participation in glycopyranosylation reactions is probed for esters at the 3-O-axial and -equatorial, 4-O-axial and -equatorial, and 6-O-sites of a range of donors through the use tert-butoxycarbonyl esters. The anticipated intermediate cyclic dioxanyl cation is interrupted for the axial 3-O-derivative, leading to the formation of a 1,3-O-cyclic carbonate ester, with loss of a tert-Bu cation, providing convincing evidence of participation by esters at that position. However, no evidence was found for such a fragmentation of carbonate esters at the 3-O-equatorial, 4-O-axial and -equatorial, and 6-O positions, indicating that neighboring group participation from those sites does not occur under typical glycosylation conditions. Further probes employing a 4-O-(2-carboxy)benzoate ester and a 4-O-(4-methoxybenzoate) ester, the latter in conjunction with an ¹⁸O quench designed to detect bridging intermediates, also failed to provide evidence for participation by 4-O-esters in galactopyranosylation.

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

Haake, M. published the artcileDialkylaminosuccinimidosulfonium compounds. 3. A simple method for the oxidation of sulfenamides to sulfinamides, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Synthesis (1979), 97, database is CAplus.

R¹SNR₂ were oxidized by treatment with N-chlorosuccinimide in CH₂Cl₂ to give a succinimidosulfonium chloride intermediate which was hydrolyzed in situ by aqueous KHCO₃ to give 41-85% R¹SONR₂ [R₂ = Me₂, (CH₂)₅, or (CH₂)₂O(CH₂)₂; R¹ = Et or Ph].

Synthesis 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

Mukherjee, Mana Mohan published the artcileSynthetic Routes toward Acidic Pentasaccharide Related to the O-Antigen of E. coli 120 Using One-Pot Sequential Glycosylation Reactions, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2017), 82(11), 5751-5760, database is CAplus and MEDLINE.

Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysaccharide of Escherichia coli 120, as its p-methoxyphenyl glycoside, have been achieved using a one-pot sequential glycosylation technique. The glycosylation have been accomplished either by the activation of the thioglycosides using NIS in the presence of FeCl₃ or by a pre-activation by Ph₂SO, TTBP, Tf₂O, and the activation of the trichloroacetimidates using FeCl₃ alone or TMSOTf. Most of the intermediate steps are high yielding, and the stereo outcomes of the glycosylation steps were excellent. The syntheses of the targeted pentasaccharide have been performed with both three- and four-component, one-pot sequential glycosylation reactions, and in both cases, the orthogonal glycosylation is carried out utilizing catalytic activity of FeCl₃. A late-stage TEMPO-mediated regioselective oxidation has been performed to achieve the required uronic acid motif.

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

Chayajarus, Kampanart published the artcileEfficient synthesis of carbohydrate thionolactones, SDS of cas: 4972-31-0, the publication is Tetrahedron Letters (2006), 47(21), 3517-3520, database is CAplus.

Carbohydrate thionolactones, e.g. I, may be efficiently synthesized from the corresponding 1-thio sugars via a two-step procedure involving formation of a glycosyl phenylthiosulfinate by treatment with either phenylsulfinyl chloride or 1-(phenylsulfinyl)piperidine (BSP), and subsequent thermal elimination in toluene.

Tetrahedron 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, SDS of cas: 4972-31-0.

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

Padungros, Panuwat published the artcileSynthesis and Reactivity of 4′-Deoxypentenosyl Disaccharides, Formula: C11H15NOS, the publication is Journal of Organic Chemistry (2014), 79(11), 4878-4891, database is CAplus and MEDLINE.

4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4′-deoxypentenosyl (4′-DP) disaccharides, and we investigate their post-glycosylation C₅‘ additions using the DMDO oxidation/ring-opening sequence. The α-linked 4’-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf₂O activation, whereas β-linked 4′-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4′-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal L-iduronic acids via the syn addition of 2-furyl-zinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochem. configuration of the terminal 4′-DP unit is established at a post-glycosylation stage.

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

Wallace, Michael D. published the artcileRed Algal Molecules – Synthesis of Methyl Neo-β-carrabioside and Its S-Linked Variant via Two Synthetic Routes: A Late Stage Ring Closure and Using a 3,6-Anhydro-D-galactosyl Donor, SDS of cas: 4972-31-0, the publication is Journal of Organic Chemistry (2020), 85(24), 16182-16195, database is CAplus and MEDLINE.

Me neo-β-carrabioside has been synthesized for the first time, employing either a late stage ring closure to install the required 3,6-anhydro-bridge or a suitable 3,6-anhydro-galactosyl donor to form the unfavored 1,2-cis-equatorial α-linkage. Using the late stage ring closure approach, an S-linked analog of Me neo-β-carrabioside was also realized. These compounds have applications in the identification and characterization of marine bacterial exo-α-3,6-anhydro-D-galactosidases that have specific activity on red algal neo-carrageenan oligosaccharides, such as those found in both family 127 and 129 of the glycoside hydrolases. In addition a biochem. assay using the synthesized Me neo-β-carrabioside and the marine bacterial exo-α-3,6-anhydro-D-galactosidase ZgGH129 demonstrates that the min. substrate unit for the enzyme is neo-β-carrabiose.

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 C24H12, SDS of cas: 4972-31-0.

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

Tresse, Cedric published the artcileTotal synthesis of tiacumicin B: study of the challenging β-selective glycosylations, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2021), 27(16), 5230-5239, database is CAplus and MEDLINE.

We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycon and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycon delivery. The rhamnosylated C1-C3 fragment was anchored to the C4-C19 aglycon fragment by a Suzuki-Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semi-glycosylated aglycon that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B.

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 C12H16O3, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Herbrandson, Harry F. published the artcileDerivatives of aromatic sulfinic acids. II. The reaction of thionyl chloride with sulfinic esters, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (1956), 2576-8, database is CAplus.

cf. C.A. 49, 9370i. PhSOCl (22.5 g.) added to 11.1 g. dry pyridine and 5 g. absolute MeOH in 60 cc. dry Et₂O, the mixture kept at -10° until no more precipitate was formed, and diluted with H₂O, the Et₂O layer washed, dried, and evaporated, and the residue distilled yielded 14.0 g. PhSO₂Me (I), b_0.04 67-8°, b_0.03 63°, n_D²⁰ 1.5400. In the same manner was prepared p-MeC₆H₄SO₂Me (II), 91%, b_0.001 68°, n_D²⁰ 1.5380. II (20.1 g.) and 14.0 g. pure SOCl₂ kept a few days in the dark and distilled gave 3.5 g. ClCO₂Me, b. 104-6°, n_D²⁰ 1.4629, and 18.7 g. p-MeC₆H₄SOCl, lemon-yellow oil, b_0.012 79°, n_D²⁰ 1.6007; it gave with NH₃ in dry Et₂O the p-MeC₆H₄SONH₂, m. 120-20.5° (from aqueous EtOH). I gave in the same manner 84% PhSOCl, yellow oil, b_0.012 65° [PhSONH₂, m. 122° (from aqueous EtOH); piperidide, m. 82-3° (from petr. ether)]. l-Menthyl 1-p-toluenesulfinate (III), m. 106-7° (corrected), [α]_D²⁵ -199.19° (c 2, Me₂CO), was prepared by the method of Phillips (C.A. 20, 397). Et₄NBr in H₂O treated with a slight excess Ag₂O, the mixture triturated twice, and the filtrate acidified to Congo red with 20% HCl and evaporated gave Et₄NCl (IV). A series of kinetic runs was carried out with III and SOCl₂ in PhNO₂ at 24.88 ± 0.05° (molar concentrations of IV, SOCl₂, and IV, and k × 10⁴ sec.^-1 given): 0.0554, 0.0616, 0.00093, 0.62; 0.0551, 0.0616, 0.00-213, 1.18; 0.0626, 0.0616, 0.00309, 1.68; 0.0590, 0.123, 0.00309, 1.92; 0.0516, 0.0616, 0.00425, 2.30; 0.0604, 0.0616, 0.00463, 2.06; 0.0779, 0.0616, 0.00463, 2.12; 0.0520, 0.0616, 0.00850, 3.55; 0.0409, 0.0616, 0.0106, 3.80; 0.0635, 0.0616, 0.0160, 4.28; 0.0548, 0.0492, 0.0213, 3.82; 0.0423, 0.0492, 0.0213, 4.24; 0.0774, 0.123, 0, 0; 0.0542, 0, 0.00617, 0; 0.0845, 0, 0.0213,0; 0.0663, 0, – (0.00525 HCl), 0; 0.0594, 0.0616, – (0.00525 HCl), 0; 0.0510, 0.0616, 0.00378 (MeOH), 0; 0.0408, 0.0616, – (0.0035 H₂O), 0; 0.0732, 0.0860, 0.0232, 7.30; 0.0703, 0.0860, 0.0232 + 0.1M SO₂, 7.63. In the absence of added chloride the reaction is slow; it is 1st order in ester and 1st order in added chloride ion. Trace impurities of the SOCl₂, probably mainly HCl, also affect the rate.

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, Safety of 1-(Phenylsulfinyl)piperidine.

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

Wang, Tao published the artcileUse of Lipase Catalytic Resolution in the Preparation of Ethyl (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam, Computed Properties of 1416134-49-0, the publication is Organic Process Research & Development (2018), 22(12), 1738-1744, database is CAplus.

Here we describe an efficient and cost-effective chemoenzymic synthesis of the β-lactamase inhibitor avibactam starting from com. available Et 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-Et 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate Et (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.

Organic Process Research & Development published new progress about 1416134-49-0. 1416134-49-0 belongs to piperidines, auxiliary class Piperidine,Chiral,Amine,Benzene,Amide, name is (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide, and the molecular formula is C15H21BO3, Computed Properties of 1416134-49-0.

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

Wang, Tao published the artcileA New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation, Quality Control of 1416134-49-0, the publication is Organic Process Research & Development (2018), 22(3), 267-272, database is CAplus.

An efficient synthesis of avibactam starting from com. available ethyl-5-hydroxypicolinate was completed in ten steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which are valuable precursors of the key intermediate Et (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation / sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.

Organic Process Research & Development published new progress about 1416134-49-0. 1416134-49-0 belongs to piperidines, auxiliary class Piperidine,Chiral,Amine,Benzene,Amide, name is (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide, and the molecular formula is C15H21BO2, Quality Control of 1416134-49-0.

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