Under mild conditions (Lewis acid/solvent/room temperature), the reaction of unprotected glucose, deoxyribose or xylose with hydroxylalkylthymine gives selectively nucleoside analogs with a spacer arm between sugar and base moiety. Experimental conditions (Lewis acid, solvent) for this new strategy leading to nucleoside analogs synthesis are discussed.
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http://dx.doi.org/10.1081/NCN-120039217 | DOI Listing |
Molecules
December 2024
Department of Chemistry, University of Massachusetts Boston, Boston, MA 02125, USA.
The rapidly growing glycoscience has boosted the research on the synthesis of glycans and their conjugates, which are centered on the stereoselective formation of glycosidic bonds. Compared to the mainstream acid-promoted glycosylation method that undergoes the S1 type mechanism, the basic/neutral conditions give better stereo control via the S2 mechanism. Anomeric hydroxyl group transformation, whether to form glycosidic bonds directly or to install a leaving group for later glycosylation, is key to carbohydrate synthesis, and the strategies in the stereo control of these reactions under basic/neutral conditions are summarized in this review.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Key Laboratory of Applied Chemistry of Chongqing Municipality and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Achieving catalytic asymmetric functionalization of methylenecyclopropanes (MCPs) by selective C-C bond cleavage is a notable challenge due to the intricate reaction partners involved. In this work, we report that chiral aldehyde/palladium combined catalysis enables the asymmetric functionalization of MCPs with NH-unprotected amino acid esters. This reaction proceeds through a regiospecific branched ring-opening mechanism, resulting in optically active α,α-disubstituted α-amino acid esters bearing nonconjugated terminal alkene units.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, University of Missouri, 601 S College Ave, Columbia, MO 65211, USA.
Toxic organic solvents and electrolytes, traditionally indispensable for electro-organic synthesis, are now being reconsidered. In developing more sustainable electro-organic synthesis, we've harnessed the aqueous micelles as solvents and electrolyte-like structures when deformed under an electric field. The technology is showcased in synthetically highly valued hydrodefluorination reactions of difluorinated indoles.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore.
Synthetic C-glycosides play a crucial role in molecular biology and medicine. With the surge of interest in C-glycosides and the demand to provide efforts with sufficient feedstock, it is highly significant to pursue novel methodologies to access C-glycosides in a concise and efficient manner. Here, we disclose an attractive strategy that diverges itself from conventional multistep reaction sequences involving the manipulations of protecting groups.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
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