137451-28-6Relevant academic research and scientific papers
Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides
Liu, Bing,van Mechelen, Jeanine,van den Berg, Richard J. B. H. N.,van den Nieuwendijk, Adrianus M. C. H.,Aerts, Johannes M. F. G.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.
, p. 118 - 129 (2019/01/04)
Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.
1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors
Meng, Bo,Zhu, Zhenqian,Baker, David C.
, p. 5182 - 5191 (2014/07/08)
A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.
Development of new glycosylation methodologies for the synthesis of archaeal-derived glycolipid adjuvants
Whitfield, Dennis M.,Yu, Siu H.,Dicaire, Chantale J.,Sprott, G. Dennis
scheme or table, p. 214 - 229 (2010/03/23)
To commercialize the production of glycolipid adjuvants, their synthesis needs to be both robust and inexpensive. Herein we describe a semi-synthetic approach where the lipid acceptor is derived from the biomass of the archaeon Halobacterium salinarum, an
Stereospecific synthesis of 1,2-trans-1-phenylthio-β-D-disaccharides under phase transfer catalysis
Tropper,Andersson,Grand-Maitre,Roy
, p. 734 - 736 (2007/10/02)
Peracetylated α-glycobiosyl bromides 1-5 derived from commercially available disaccharides, were transformed with complete anomeric stereocontrol into phenyl 1,2-trans-1-thio-β-D-glycobiosides 6-10 by nucleophilic displacement under phase transfer catalyz
