28140-37-6Relevant articles and documents
Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH
Adinolfi, Matteo,Iadonisi, Alfonso,Ravidà, Alessandra,Schiattarella, Marialuisa
, p. 7863 - 7866 (2003)
Peracetylated sugars can be efficiently converted into the corresponding 1,2-ethylidenes, -orthoesters, and -glycals via the in situ generation of glycosyl iodides promoted by I2/Et3SiH. The approach is straightforward and avoids isolation of the sensitive iodinated intermediates.
Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins
Wawryszyn, Mirella,Sauter, Paul F.,Nieger, Martin,Koos, Martin R. M.,Koehler, Christine,Luy, Burkhard,Lemke, Edward A.,Br?se, Stefan
, p. 4296 - 4305 (2018/08/29)
Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.
Novel approaches for the synthesis and activation of thio- and selenoglycoside donors
Valerio, Silvia,Iadonisi, Alfonso,Adinolfi, Matteo,Ravida, Alessandra
, p. 6097 - 6106 (2008/02/09)
(Chemical Equation Presented) Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.