ArticleThe Journal of organic chemistry2023
Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?
Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The use of a phenylthio group (SPh) as a dummy ligand at the 6-position to control the side-chain conformation of a series of hexopyranosyl donors is described. The SPh group limits side-chain conformation in a configuration-specific manner, which parallels that seen in the heptopyranosides, and so influences glycosylation selectivity. With both d- and l-glycero-d-galacto-configured donors, the equatorial products are highly favored as they are with an l-glycero-d-gluco donor. For the d-glycero-d-gluco donor, on the other hand, modest axial selectivity is observed. Selectivity patterns are discussed in terms of the side-chain conformation of the donors in combination with the electron-withdrawing effect of the thioacetal group. After glycosylation, removal of the thiophenyl moiety and hydrogenolytic deprotection is achieved in a single step with Raney nickel.
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