Sugar, per-O-acetylated

The classical method for introducing the fluorine atom to the anomeric center is to treat per-O-acetylated sugars with hydrogen fluoride [15], using which a-glycosyl fluorides can be prepared stereoselectively, however, the procedure is incompatible with any acid-sensitive functionalities present in the molecule. In addition, hydrogen fluoride is highly corrosive, which makes this method unattractive to many... 

The application of diazo coupling is somewhat limited by the availability of the p-aminophenyl glycosides, particularly of those of the oligosaccharides. Their precursors, the p-nitrophenyl glycosides, are usually obtained by the condensation of a per-O-acetylated glycosyl halide with p-nitrophenol in ethanol (Michael reaction)19,20 or by the reaction of a per-O-acetylated sugar with p-nitrophenol in the presence of a Lewis acid catalyst (Helferich reaction).21 p-Nitrobenzyl 1-thioglycosides have also been prepared by the condensation of the... 

Type of reaction protection Reaction condition solvent-free Keywords per-O-acetylated sugar, iodine... 

Paper ionophoresis, sugars, Maurice Stacey s work, 17 Pectic acid, 350, 352,414 Pectin, 348, 350-353 Pectinic acid, 353 Pentulose, synthesis, 281 D-cryt/iro-Pentulose 5-phosphate, 289 Peptidoglycans, 167-168 Per-O-acetylated di-D-fructose dianhydride derivatives... 

Mukhopadhyay (2006) used sulfuric acid immobilized on silica gel as the promoter for acetylation of sugar glycosides to afford the corresponding products in good to excellent yields (Scheme 5.42). Furthermore, the per-O-acetylated acetals/ ketals were successfully synthesized by this method. 

Glycosyl fluorides have also been prepared by treatment of per-O-acyl or partially 0-acylated sugars with hydrogen fluoride [liquid HF (for example, see Refs. 38 and 39) or HF in acetic acid or dichloromethane], as exemplified by 2,3,4-tri-O-benzyl-a-D-xylopyranosyl (18), a-D-glucopyranosyl (19), tetra-O-pivaloyl-a-D-glucopyranosyl (20), and 2,3,5-tri-O-acetyl-D-xylofur-anosyl fluorides (21) (see Table 1). Frequently, HF treatment - leads to... 

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