20701-64-8Relevant academic research and scientific papers
One-Pot Relay Glycosylation
Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing
supporting information, p. 5498 - 5503 (2020/04/09)
A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.
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
SYNTHETIC ARCHAEAL GLYCOLIPID ADJUVANTS
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Page/Page column 27, (2008/06/13)
Archaeal lipid adjuvants are synthesized by chemically coupling various carbohydrates or anionic polar groups to the free hydroxyl(s) of archaeal lipid cores. Chemically stable lipid cores such as saturated archaeol and caldarchaeol are obtained from appr
Synthesis of a hexasaccharide fragment of the capsular polysaccharide of streptococcus pneumoniae type 3
Lefeber, Dirk J.,Aldaba Arevalo, Eneko,Kamerling, Johannis P.,Vliegenthart, Johannes F.G.
, p. 76 - 81 (2007/10/03)
In the framework of the development of a new generation of neoglycoconjugate vaccines against Streptococcus pneumoniae, the synthesis is described of a spacer-containing hexasaccharide fragment related to the capsular polysaccharide of S. pneumoniae type
Rapid carbohydrate protecting group manipulations assisted by microwave dielectric heating
Soederberg, Eva,Westman, Jacob,Oscarson, Stefan
, p. 397 - 410 (2007/10/03)
The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.
Nucleophile Induced Rearrangements of Thioglycosides: Formation of 6-Thio Glycosides and 1,6 Thioanhydrosugars
Lowary, Todd L.,Bundle, David R.
, p. 2397 - 2404 (2007/10/02)
Treatment of Ethyl 2,3 di-O-benzoyl-4,6-di-O-toluenesulfonyl-1-thio-β-D-glucopyranoside 12 with sodium methoxide at low temperature gives Methyl 3,4 anhydro-6-S-ethyl-β-D-galactopyranoside 13, whereas treatment with sodium iodide in refluxing butanone yie
