Darstellung von amino zuckern durch hydroxyaminierungsreaktionen an ungesattigten kohlenhydraten

Heyns, Kurt; Feldmann, J.

doi:10.1016/s0040-4039(01)83074-4

Cited by 8 publications

(1 citation statement)

References 7 publications

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“…Amidation of glucal derivatives, meanwhile, offers unique opportunities for 2-amino-2-deoxy-mannopyranoside synthesis but presents the challenge of incorporating the C2 nitrogen cis to the C3 oxygen substituent (or vice versa) . In addition to stereocontrol at the nitrogen-bearing center, glucal amidation methodology should also permit stereoselective incorporation of anomeric substituents and streamlined elaboration to ManNAc-type products.…”

Section: Introductionmentioning

confidence: 99%

α-N-Acetylmannosamine (ManNAc) Synthesis via Rhodium(II)-Catalyzed Oxidative Cyclization of Glucal 3-Carbamates

et al. 2005

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[reaction: see text] Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh2(OAc)4, providing mannosamine 2-N,3-O-oxazolidinones. With iodosobenzene, incorporation of 4-penten-1-ol provided a readily separable anomeric mixture of n-pentenyl glycosides, with the anomers exhibiting pronounced differences in reactivity as glycosyl donors. N-acylation of the sugar oxazolidinones led to alpha-selective glycosyl donors for the elaboration of various 2-mannosamine frameworks. Alternatively, the anomeric n-pentenyl glycosides of N-Cbz 2-mannosamine oxazolidinones were converted separately to oxazolidinone-opened derivatives 28alpha and 28beta. These served as stereoconvergent glycosyl donors, and the alpha-linked products were readily advanced to a variety of N-acetylmannosamine (ManNAc) frameworks, using an intramolecular O-->N acetyl transfer as the final step.

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Section: Introductionmentioning

confidence: 99%