79698-05-8Relevant articles and documents
Practical synthesis of 2-deoxy sugars via metal free deiodination reactions
Wan, Qian,Wang, Hao,Yao, Wang,Zeng, Jing
, (2022/01/20)
2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b
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
, 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.
Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination
Wang, Hao,Tao, Jinyi,Cai, Xinpei,Chen, Wei,Zhao, Yueqi,Xu, Yang,Yao, Wang,Zeng, Jing,Wan, Qian
, p. 17319 - 17323 (2015/02/19)
2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-a-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasac-charide containing four a-linkages.
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.]
Recent advances in the synthesis of 2-deoxy-glycosides
Hou, Dianjie,Lowary, Todd L.
scheme or table, p. 1911 - 1940 (2010/03/01)
Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.; Franck, R. W. Tetrahedron 2000, 56, 8385-8417).
CeCl3·7H2O: A novel reagent for the synthesis of 2-deoxysugars from D-glycals
Yadav,Reddy,Reddy, K.Bhaskar,Satyanarayana
, p. 7009 - 7012 (2007/10/03)
D-Glycals react smoothly with a variety of alcohols in a highly stereoselective manner in the presence of the CeCl3·7H2O-NaI reagent system in refluxing acetonitrile under neutral conditions to afford the corresponding 2-deoxy-α-glycopyranosides in high yields. In the absence of NaI, the glycals undergo Ferrier rearrangement under the influence of CeCl3·7H2O in refluxing acetonitrile to afford the corresponding 2,3-unsaturated hexopyranosides in good yields.
