A general method for alpha-selective glycosylation with 5-thioglucopyranosyl donors followed by efficient deprotection of the resulting products was developed. This methodology was utilized in the synthesis of an isomaltotetraoside analogue.
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Stereoselective Glycosylation for 1,2--Aminoglycoside Assembly by Cooperative Atom Transfer Catalysis.
J Am Chem Soc
December 2024
Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States.
We report here a new catalytic method for exclusively 1,2--α-selective glycosylation that assembles a wide variety of 1,2--aminoglycosidic linkages in complex glycans and glycoconjugates. Mechanistic studies revealed a unique glycosylation mechanism in which the iron catalyst activates a glycosyl acceptor and an oxidant when it facilitates the cooperative atom transfer of both moieties to a glycosyl donor in an exclusively -selective manner. This catalytic approach is effective for a broad range of glycosyl donors and acceptors, and it can be operated in a reiterative fashion and scaled up to the multigram scale.
View Article and Find Full Text PDFZinc(ii)-mediated stereoselective construction of 1,2- 2-azido-2-deoxy glycosidic linkage: assembly of K48 capsular pentasaccharide derivative.
Chem Sci
August 2024
School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University Shenzhen 518107 China
The capsular polysaccharide (CPS) is a major virulence factor of the pathogenic and a promising target for vaccine development. However, the synthesis of the 1,2--2-amino-2-deoxyglycoside core of CPS remains challenging to date. Here we develop a highly α-selective ZnI-mediated 1,2- 2-azido-2-deoxy chemical glycosylation strategy using 2-azido-2-deoxy glucosyl donors equipped with various 4,6--tethered groups.
View Article and Find Full Text PDFα-Selective Solid-Phase Synthesis of Glycosyl Phosphate Repeating Structure Via the Phosphoramidite Method.
Chemistry
October 2024
Department of Medicinal and Life Sciences, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda Chiba, 278-8510, Japan.
Lipophosphoglycans (LPGs) are found on the surface of Leishmania, a protozoan parasite, and are immunologically important. Herein, disaccharide 1-phosphate repeating units of LPGs were successfully synthesized on a solid support with high anomeric purity using a disaccharide α-1-phosphoramidite building block. To enhance solubility in the reaction solvent, hydroxy-protecting groups in the form of para-t-butylbenzoyl were introduced to the building block.
View Article and Find Full Text PDFStereoselective Entry into α,α'-C-Oxepane Scaffolds through a Chalcogen Bonding Catalyzed Strain-Release C-Septanosylation Strategy.
Angew Chem Int Ed Engl
July 2024
Abteilung Chemische Biologie, Max Planck Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227, Dortmund, Germany.
The utility of unconventional noncovalent interactions (NCIs) such as chalcogen bonding has lately emerged as a robust platform to access synthetically difficult glycosides stereoselectively. Herein, we disclose the versatility of a phosphonochalcogenide (PCH) catalyst to facilitate access into the challenging, but biologically interesting 7-membered ring α,α'-C-disubstituted oxepane core through an α-selective strain-release C-glycosylation. Methodically, this strategy represents a switch from more common but entropically less desired macrocyclizations to a thermodynamically favored ring-expansion approach.
View Article and Find Full Text PDFStereocontrolled synthesis of α-d-allulofuranosides using α-selective d-fructofuranosidation reaction.
Carbohydr Res
February 2024
Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, 852-8521, Japan. Electronic address:
Stereocontrolled synthesis of rare sugar derivatives, namely α-d-allulofuranosides, was achieved using d-fructose, one of the most abundant carbohydrates in nature. The following are the key steps of the α-d-allulofuranosides' synthesis. (1) An α-selective glycosidation reaction of 1,3,4,6-tetra-O-benzoylated d-fructofuranosyl donor to obtain α-d-fructofuranosides with 98 %-75 % isolated yields.
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