Glycoside nitromethyl

The formation of nitroalkyl glycosides, illustrated in Figure 7.12, is limited in scope and few examples have been reported. The problems associated with this reaction involve the acidity of nitromethyl groups. Specifically, after formation of the C-glycoside, nitromethyl anions are easily formed. Moreover, when acetyl protecting groups are used, nitronates readily form. The few examples illustrated in this section are intended to convey the relatively limited accessibility of these compounds. 

Addition reactions. CAN serves as a catalyst for the conjugate addition of thiols and selenols to enones under solvent-free conditions. Glycals are transformed into glycosides containing a nitromethyl group at C-2. ... 

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