Biomaterial Database

Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts. 2020

Kumar Bhaskar Pal, and Jiande Lee, and Mrinmoy Das, and Xue-Wei Liu

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371. xuewei@ntu.edu.sg.

An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.

UI	MeSH Term	Description	Entries
D010165	Palladium	A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D011134	Polysaccharides	Long chain polymeric CARBOHYDRATES composed of MONOSACCHARIDES linked by glycosidic bonds.	Glycan,Glycans,Polysaccharide
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D004988	Ethers, Cyclic	Compounds of the general formula R-O-R arranged in a ring or crown formation.	Cyclic Ether,Cyclic Ethers,Ether, Cyclic
D006027	Glycosides	Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed)	Glycoside
D006031	Glycosylation	The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION).	Protein Glycosylation,Glycosylation, Protein
D012492	Salts	Substances produced from the reaction between acids and bases; compounds consisting of a metal (positive) and nonmetal (negative) radical. (Grant & Hackh's Chemical Dictionary, 5th ed)	Salt
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer