69247-28-5Relevant articles and documents
Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1- thioglycosides
Paul, Somak,Jayaraman, Narayanaswamy
, p. 2197 - 2204 (2004)
Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Glycosylation reactions of the thioglycosides with both aglycosyl and glycosyl acceptors afford α-anomeric glycosides exclusively. Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and α-anomeric 2-deoxy glycosides were obtained exclusively.
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
Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester
Manhas, Sanjay,Taylor, Mark S.
, p. 42 - 49 (2018/10/26)
An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C–O bond formation from carbohydrate-derived hemiacetals.
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.]
