64694-19-5Relevant articles and documents
Ferrocenium complex aided: O-glycosylation of glycosyl halides
Bauer, Eike B.,Talasila, Deva Saroja
, p. 36814 - 36820 (2021/12/02)
A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)2]SbF6 and FcBF4 as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load). This journal is
Indolylthio glycosides as effective building blocks for chemical glycosylation
Demchenko, Alexei V.,Shrestha, Ganesh,Panza, Matteo,Singh, Yashapal,Rath, Nigam P.
, p. 15885 - 15894 (2021/01/19)
The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.
Reagent Controlled Stereoselective Assembly of α-(1,3)-Glucans
Wang, Liming,Overkleeft, Herman S.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
, p. 1994 - 2003 (2018/10/15)
Pre-activation based glycosylations have become a very powerful tool in the assembly of oligosaccharides and the use of nucleophilic additives allows for the in situ generation of reactive intermediates with tailored reactivity. We here use a glycosylation strategy that is based on the use of per-benzylated imidate building blocks for the fully stereoselective construction of a spacer equipped Aspergillus fumigatus α-1,3-octaglucan. We have used the trimethylsilyl iodide (TMSI)-triphenylphosphine oxide (Ph3P=O) for the stereoselective installation of an azidopropanol spacer and triflic acid (TfOH)-dimethyl formamide (DMF) enabled glycosylations for the coupling reactions with the secondary glucosyl C-3-alcohols. An operationally simple in situ activation coupling procedure is introduced and used for the final glycosylation events towards the octasaccharide.