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Involvement of an Oxonium Ion Intermediate in Controlling the Diastereoselectivity of Nucleophilic Substitution Reactions of Septanoses.
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ABSTRACT:
SUBMITTER: Luu KB
PROVIDER: S-EPMC9850862 | biostudies-literature | 2023 Jan
REPOSITORIES: biostudies-literature
Publications
Involvement of an Oxonium Ion Intermediate in Controlling the Diastereoselectivity of Nucleophilic Substitution Reactions of Septanoses.
Organic letters 20230104 1
The alkoxy substituents at C4 and C2 of septanoses control the stereochemical outcomes of <i>O</i>-glycosylation reactions of these seven-membered-ring intermediates. Isolation of a bicyclic acetal byproduct in some substitution reactions suggests that the C4 benzyloxy substituent engaged in long-range participation, stabilizing intermediates by the formation of an oxonium ion intermediate. Inductive destabilization of the carbocationic intermediate provided by the C2 substituent is crucial to t ...[more]