69247-26-3Relevant academic research and scientific papers
Bismuth-Catalyzed Stereoselective 2-Deoxyglycosylation of Disarmed/Armed Glycal Donors
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj,Kumar, Nitin
supporting information, p. 575 - 580 (2022/01/28)
Bi(OTf)3 promoted direct and highly stereoselective glycosylation of “disarmed” and “armed” glycals to synthesize 2-deoxyglycosides has been reported. The tunable and solvent-controlled chemoselective activation of deactivated glycal donors dis
Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated d-galactal
Tatina, Madhu Babu,Moussa, Ziad,Xia, Mengxin,Judeh, Zaher M. A.
supporting information, p. 12204 - 12207 (2019/10/22)
Perfluorophenylboronic acid 1c catalyzes the direct stereoselective addition of alcohol nucleophiles to deactivated peracetylated d-galactal to give 2-deoxygalactosides in 55-88% yield with complete α-selectivity. The unprecedented results reported here a
α-Selective synthesis of 2-deoxy-glycosides and disaccharides
Yang, Guofang,Luo, Xiaosheng,Guo, Hong,Wang, Qingbing,Zhou, Jiafen,Huang, Tianyun,Tang, Jie,Shan, Junjie,Zhang, Jianbo
, p. 128 - 152 (2018/03/26)
A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0°C to form glycosides, glycoconjugates, and disaccharides with excellent α-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.
TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
Hsu, Mei-Yuan,Liu, Yi-Pei,Lam, Sarah,Lin, Su-Ching,Wang, Cheng-Chung
supporting information, p. 1758 - 1764 (2016/10/05)
The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
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.]
Building Units of Oligosaccharides, CII. - Synthesis of Modified Derivatives of 2-Acetamido-2-deoxy-D-galactose for the Examination of Substrate Specifities of Core 1-β3-Gal-Transferase and Core 3-β3-GlcNAc-Transferase Involved in the Biosynthesis of O-Gl
Paulsen, Hans,Rutz, Volker,Brockhausen, Inka
, p. 735 - 746 (2007/10/02)
The 2-, 3-, 4-, and 6-deoxy derivatives of benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (7) have been synthesized to test substrate specifities of glycosyltransferases involved in the biosynthesis of O-glycoproteins.The core 1-β3-Gal-transferase does
