Tresse, Cedric published the artcileTotal synthesis of tiacumicin B: study of the challenging β-selective glycosylations, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2021), 27(16), 5230-5239, database is CAplus and MEDLINE.
We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycon and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycon delivery. The rhamnosylated C1-C3 fragment was anchored to the C4-C19 aglycon fragment by a Suzuki-Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semi-glycosylated aglycon that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B.
Chemistry – A European Journal published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C12H16O3, Recommanded Product: 1-(Phenylsulfinyl)piperidine.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
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