Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• introduced by Kusumoto et al. [46], however, this term was coined by the same group much later [51]. We adopt this term to generally refer to this concept, which in other applications was also named “intramolecular glycosylation of prearranged glycosides” by Ziegler [52][53], “template-directed cyclo

• tethers Ziegler and co-workers investigated the use of a flexible succinoyl linker to link the glycosyl donor and acceptor counterpart. This reaction was named “intramolecular glycosylation of prearranged glycosides” [52][53]. Like in all “molecular clamp” applications, the tethering of the reaction

• . First intramolecular glycosylation using the molecular clamping. Succinoyl as a flexible linker for intramolecular glycosylation of prearranged glycosides. Template-directed cyclo-glycosylation using a phthaloyl linker. Phthaloyl linker-mediated synthesis of branched oligosaccharides via remote

Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size

• Patrick Claude,
• Christian Lehmann and
• Thomas Ziegler

Beilstein J. Org. Chem. 2011, 7, 1609–1619, doi:10.3762/bjoc.7.189

• glucosyl moieties was mainly responsible for the observed regioselectivity and anomeric selectivity of the ring-closing glycosylation step. Keywords: intramolecular glycosylation; molecular modeling; prearranged glycosides; Introduction Intramolecular O-glycosidic bond formation of tethered glycosyl

• donors and acceptors (prearranged glycosides) resembles to some extent enzyme-catalyzed glycosylation reactions where the glycosyl donor and glycosyl acceptor are first bound in the active site of an enzyme and thus, the glycosidic bond forms intramolecularly. Three different concepts for the

• mannosylations that double diastereodifferentiation is responsible in part for the anomeric selectivity of such intramolecular glycosylations, although the exact cause of this effect has not been unambiguously identified so far [27]. Therefore, we prepared a series of prearranged glycosides constructed out of a