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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 o...
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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癈 to form glycosides, glycoconjugates, and disaccharides with excellent ?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.
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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 summ...
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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).
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2-Deoxy-2-iodopyranosides 3, and 9-12 were synthesized from sulfanyl alkenes using a "one pot" consecutive cyclization-glycosylation process. Compared with the stepwise procedure, the "one pot" process gave significantly improved ...
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2-Deoxy-2-iodopyranosides 3, and 9-12 were synthesized from sulfanyl alkenes using a "one pot" consecutive cyclization-glycosylation process. Compared with the stepwise procedure, the "one pot" process gave significantly improved yields with similar or slightly lower selectivities. The "one pot" procedure was applied to the synthesis of 2,6-dideoxy-2-iodoglycoside 22, which was successfully deiodinated to afford the 2,6-dideoxyglycoside 23. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
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1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-a-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline...
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1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-a-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from D-glucal, D-galactal, and D-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.
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Several 2-deoxy-alpha-D-glucopyranosides are stereoselectively synthesized in high yields by glycosylation of various alcoholic nucleophiles with 3,4,6-tri-O-benzyl-2-deoxy-glucopyranose using a catalytic amount of trityl tetrakis...
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Several 2-deoxy-alpha-D-glucopyranosides are stereoselectively synthesized in high yields by glycosylation of various alcoholic nucleophiles with 3,4,6-tri-O-benzyl-2-deoxy-glucopyranose using a catalytic amount of trityl tetrakis(pentafluorophenyl) berate. [References: 20]
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A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy α- glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2- deoxy a...
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A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy α- glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2- deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford α-selective glycosides in good to excellent yields.
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This report provides an overview of the recent synthetic efforts directed toward the assembly of complex 2-deoxy-beta-glycoside-containing natural products landomycin A, apoptolidin A, digitoxin, lomaiviticin A, incednine, and ver...
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This report provides an overview of the recent synthetic efforts directed toward the assembly of complex 2-deoxy-beta-glycoside-containing natural products landomycin A, apoptolidin A, digitoxin, lomaiviticin A, incednine, and versipelostatin. In particular, the intention of this review is to cover the work published since the earlier reports on this topic by Lowary and Hou (2009) and Franck and Marzabadi (2000).
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This paper addresses the existence and role of a catalytic nucleophile in retaining glycoside hydrolases and retaining glycosyl transferases.Although the former has new been established beyond douby,such is not the case with the l...
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This paper addresses the existence and role of a catalytic nucleophile in retaining glycoside hydrolases and retaining glycosyl transferases.Although the former has new been established beyond douby,such is not the case with the latter.We report reliable procedures for the synthesis of various 2-deoxy-2-fluoro glycosyl nucleoside diphosphates,useful donor analogues for the study for the mechanism of action of retaining glycosyl transferases.
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Y 2-Deoxy sugars exist in numerous bioactive molecules and exert significant influences on their physical, chemical, and biological properties. Due to the absence of directing group at C-2 and the labile nature of glycosidic linka...
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Y 2-Deoxy sugars exist in numerous bioactive molecules and exert significant influences on their physical, chemical, and biological properties. Due to the absence of directing group at C-2 and the labile nature of glycosidic linkages, stereoselective construction of 2-deoxy glycosides is rather challenging. Despite the fact that remarkable success in the synthesis of 2-deoxy sugars were achieved using indirect routes, direct synthesis of 2-deoxy glycosides has been extensively explored in order to improve overall synthetic efficiency through eliminating extra pre- and post-glycosylation steps. In this account, we have summarized advances in direct synthesis of 2-deoxy glycosides reported in the last decade, with an emphasis on those efforts published in last five years. In addition, some recent reports in stereoselective synthesis of 2-deoxy thioglycosides have also been discussed. (C) 2021 Elsevier Ltd. All rights reserved.
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