3427-20-1Relevant academic research and scientific papers
Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides
Alami, Mouad,Franco, Rémi,Gandon, Vincent,Ghouilem, Juba,Messaoudi, Samir,Retailleau, Pascal
supporting information, p. 7175 - 7178 (2020/07/14)
An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.
Selective Synthesis of Some Aminosugars via Catalytic Aminohydroxylation of Protected 2,3-Unsaturated d -Gluco- And d -Galacto-2-hexenopyranosides
Fukuhara, Ippei,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 9179 - 9189 (2020/08/14)
The aminohydroxylation of methyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-unsaturated α-d-glucopyranoside proceeds in the presence of chloramine-T, OsO4 (4 mol %), (DHQ)2PHAL (5 mol %), and triethylbenzylammonium chloride (TEBAC) in both a stereoselective a
Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions
Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna
, p. 1385 - 1387 (2020/06/27)
Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.
Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization
Fukaya, Keisuke,Tanaka, Yuta,Sato, Ayako C.,Kodama, Keisuke,Yamazaki, Hirohisa,Ishimoto, Takeru,Nozaki, Yasuyoshi,Iwaki, Yuki M.,Yuki, Yohei,Umei, Kentaro,Sugai, Tomoya,Yamaguchi, Yu,Watanabe, Ami,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
supporting information, p. 2570 - 2573 (2015/06/16)
A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.
Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones
Chittela, Sravanthi,Reddy, Thurpu Raghavender,Radha Krishna, Palakodety,Kashyap, Sudhir
, p. 7108 - 7116 (2015/07/28)
An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.
Linearization of carbohydrate derived polycyclic frameworks
Singh, Priyanka,Panda, Gautam
, p. 31892 - 31903 (2014/08/18)
We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.
Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst
Rosati, Ornelio,Curini, Massimo,Messina, Federica,Marcotullio, Maria Carla,Cravotto, Giancarlo
, p. 169 - 175 (2013/03/13)
Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]
Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
Freitas, Juliano C. R.,Couto, Tulio R.,Paulino, Antonio A. S.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.,De Freitas Filho, Joao R.
, p. 10611 - 10620,10 (2012/12/12)
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols
Williams, D. Bradley G.,Simelane, Sandile B.,Kinfe, Henok H.
supporting information; experimental part, p. 5636 - 5642 (2012/08/07)
A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st
Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
Freitas, Juliano C.R.,Couto, Túlio R.,Paulino, Ant?nio A.S.,De Freitas Filho, Jo?o R.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.
, p. 8645 - 8654 (2012/10/29)
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
