Synthetic Route of C9H11Cu. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Mesitylcopper(I), is researched, Molecular C9H11Cu, CAS is 75732-01-3, about An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed Stereo-divergent Propargylation of Unprotected Aldoses. Author is Wei, Xiao-Feng; Shimizu, Yohei; Kanai, Motomu.
We developed a copper(I)-catalyzed stereo-divergent anomeric propargylation of unprotected aldoses as a facile synthetic pathway to a broad variety of sialic acid derivatives The soft allenyl-copper(I) species, catalytically generated from stable allenyl-boronic acid pinacolate, is unusually inert to protonolysis by the multiple hydroxy groups of the substrates and thereby functions as a carbon nucleophile. The key additive B(OMe)3 facilitated ring-opening of the non-electrophilic cyclic hemiacetal forms of aldoses to the reactive aldehyde forms. The chirality of the catalyst, and not the internal stereogenic centers of substrates, predominantly controlled the stereochem. of the propargylation step; i.e., the diastereoselectivity was switched simply by changing the catalyst chirality. This is the first non-enzyme catalyst-controlled stereo-divergent C-C bond elongation at the anomeric center of unprotected aldoses, which contain multiple protic functional groups and stereogenic centers. The propargylation products can be expeditiously transformed into naturally occurring and synthetic sialic acid derivatives in a simple three-step sequence. This synthetic method, which requires no protecting groups, can be performed on a gram-scale and thus offers general and practical access to various sialic acid derivatives from unprotected aldoses.
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