Synthesis of a useful lauryl thioglycoside of sialic acid and its application

Pre-activation of fully acetylated dodecyl thioglycosides with BSP–Tf2O led to efficient glycosylation at low temperature

“…We have demonstrated previously that dodecyl thioglycosides of glucose 6 and N-acetylneuraminic acid 7 showed excellent reactivity as glycosyl donors. 6b, 6c It is well known that thioglycosides having O-benzoyl or O-pivaloyl groups at their 2-positions afford the corresponding 1,2-trans glycosides through neighboring group participation.…”

“…9 In order to extend synthetic utility of acetylated thioglycosyl donors, we re-investigated their glycosylation using various thiophilic reagents so far reported. In the course of our studies in oligosaccharide synthesis, 6,7 we focused 6b, 6c…”

Tunable stereoselectivity during sialylation using an N-acetyl-5-N,4-O-oxazolidinone-protected p-toluene 2-thio-sialoside donor with Tf2O/Ph2SO/TTBPy

“…These structures play significant biological roles in higher animals and human beings. [1][2][3][4][5] Over the years, tremendous efforts have been made to develop sialic acid donors for efficient a-selective sialylation, [6][7][8][9][10][11][12] including the use of anomeric leaving groups at C-2, such as halides, 6,[13][14][15][16] sulfide, [17][18][19] xanthate, 20,21 phosphite/phosphate, [22][23][24] and trifluoroacetimidate, 25 as well as the incorporation of an auxiliary group at C-1 [26][27][28][29][30][31] and C-3 [32][33][34][35][36][37] ; the modification of the amino protective groups at C-5. 38 Recently, 5-N,4-O-oxazolidinone as a protective group for 2-thiosialoside donors was introduced by several research groups, [39][40][41][42][43][44][45]…”