Glycosyl fluorides glycoside synthesis

Table 2.2 Synthesis of 1,2-c/s-glycosides by using glycosyl fluorides as glycosyl donors promoted by SnCI2-AgCI04 [6] or SnCI2-TrCI04 [7],...

Glycosyl fluorides, widely used reagents in carbohydrate and natural product chemistry,745 746 can be used to carry out stereoselective synthesis of glycosides with a catalytic amount (5 mol%) of triflic acid. The appropriately protected /3-D-glycosyl fluorides of glucose and galactose as donor molecules, when applied in dichloro-... 

Friedel-Crafts alkylation has been used in an important synthesis of aryl C-glycosides, which are potent anti-tumor agents, from glycosyl fluorides (equation 99)65 661. The reaction takes place rapidly in dichloromethane, at room temperature using a novel zirconium complex and silver perchlorate combination catalyst. A similar alkylation has been performed by replacing the aromatic compound with either a silyl enol ether or an allylic compound using silver triflate as the catalyst662,663. 

Not within the scope of this section are the synthesis of a-fluoro sulfides from dithioace-tals, their reduction to alkyl fluorides, and the synthesis of glycosyl fluorides from (phenyl-sulfanyl)glycosides. ... 

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