Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes

A practical and scalable synthesis of KRN7000 using glycosyl iodide as the glycosyl donor

“…30 Others have used optimized methods to synthesize several other α-GalCers, 31 C-linked sugars, 32 oligosaccharides, and glycoconjugates which present potential applications as cancer vaccines or as adjuvant candidates. 33 Due to the long-term interest in their relevant biological properties, our group has focused on the syntheses of α-GalGSLs for many years 22,24,25,34 and have tried to develop a practical and scalable synthetic procedure for KRN7000 and its analogues. In view of the advantages of the galactosyl iodide strategy expressed in the synthesis of the α-GalCers, we decided to investigate this technique.…”

Chemistry and Biology of Bioactive Glycolipids of Marine Origin

“…The first total synthesis of a clarhamnoside member ( 117a 2 b 6 ) was carried out by Li et al [ 58 ]. According to this work, the glycosylation reaction between 118 and 119 , promoted by the NIS/AgOTf system, afforded a 3:1 α:β separable mixture of the disaccharide 120 in 76% yield.…”

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

“…After the disclosure of the structure 1 by Kirin Brewery, 4) many reports on the synthesis of 1 were published from 1995 to 2011, [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] including practical synthesis of it by Kirin group. 25) As shown in Fig.…”

“…Hence the synthesis of 1 includes two key steps: -selective (or -specific) galactosylation, and the construction of three continuous asymmetric centers of the phytosphingosine chain. To connect a galactose part in -orientation, researchers have used 1-OH free garactopyranose (D), 30,33,44) thiogalactoside (E), 28,30,36,37,41) galactosyl trichloroacetimidate (F), [27][28][29][32][33][34]36,39,43) phosphite (G), 33) phosphate (H), 42) acetate (I), 37) or halide (J) as the galactose donor. 4,25,26,29,31,35,38,40) Hague, 31) and trichloroacetimidate (L) with trimethylsilyl triflate (60%) reported by Kimura et al, 32) gave the highest -stereoselectivity (exclusivity).…”