Stereocontrolled glycosyl transfer reactions with unprotected glycosyl donors.

Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O‐Glycosylation of 1‐O‐Acetyl Sugars as Glycosyl Donors

Synthesis of a LEC14 nonasaccharide, a core-fucosylated, biantennary N-glycan with a novel GlcNAc residue in the core region

In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy­droxy­methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) A. There are two intra­molecular hydrogen bonds (O—H⋯N and N—H⋯O) between the hy­droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl­prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol­ecules are connected into a dimer by an O—H⋯O hydrogen bond. The dimers are further linked by N—H⋯O, C—H⋯N and C—H⋯O inter­actions, extending a sheet structure parallel to (\overline{1}01).

https://journals.iucr.org/e/issues/2016/03/00/is5442/is5442.pdf

Roland Haeckel

Papers

Synthesis of Unprotected O-Glycosyl Trichloroacetimidates Structure Assignment and New Results

Synthesis of Unprotected O‐Glycosyl Trichloroacetimidates. Structure Assignment and New Results.