378
2
General Synthetic Methods
⊡ Figure 1
Glycosidesubstrates for nucleophilic hydrolysis
⊡ Scheme 1
anomeric ethyl glycoside derivatives 17 and 18 as well as the diastereoisomeric acetal 19
and 20 have been studied kinetically. The time-dependent distribution of the acetolysis products from 17 and 18 shows that their rapid mutual anomerization precedes their acetolysis
to 21 and 22, undoubtedly by way of the endo-cyclic cleavage product 23, the precursor of 19
and 20 [14] ( > Fig. 2).
2
General Synthetic Methods
⊡ Figure 1
Glycosidesubstrates for nucleophilic hydrolysis
⊡ Scheme 1
anomeric ethyl glycoside derivatives 17 and 18 as well as the diastereoisomeric acetal 19
and 20 have been studied kinetically. The time-dependent distribution of the acetolysis products from 17 and 18 shows that their rapid mutual anomerization precedes their acetolysis
to 21 and 22, undoubtedly by way of the endo-cyclic cleavage product 23, the precursor of 19
and 20 [14] ( > Fig. 2).