Reagent Controlled Synthesis of 1,2-cis-Oligosaccharides

Wang, L. (2020)

Doctoral Thesis

This Thesis describes a strategy to synthesize 1,2-cis-oligosaccharides modulated by additives, such as dimethylformamide (DMF), triphenylphosphine oxide (Ph3P=O) and N-methyl(phenyl)formamide (MPF), using building blocks that carry solely benzyl type protecting groups and are therefore of uniform reactivity. These three additives were used for different classes of donor-acceptor combinations. The additive DMF was mainly used to modulate glycosylations of per-benzylated glucosyl donors and secondary alcohol acceptors. The TMSI-Ph3P=O condition was used to glycosylate the more reactive primary alcohol acceptors. The MPF additive, which forms less stable anomeric imidinium ion intermediates than DMF, was used for donors that are somewhat less reactive, such as those in the 2-azido-2-deoxy series.

• Additive
• 1,2-cisglycosylation
• glucan
• DMF
• TMSI-PH3P=O
• MPF
• Galactosylation
• 2-azido-sugar

• All authors: Wang, L.
• Supervisor: Marel, G.A. van der; Codée, J.D.C.
• Committee: Overkleeft, H.S.; Brouwer, J.; Artola, M.E.; Boons, G.J.; Ye, X.-S.
• Qualification: Doctor (dr.)
• Awarding Institution: Leiden Institute of Chemistry (LIC), Faculty of Science, Leiden University
• Date: 2020-02-25