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Ether Protecting Groups Notes

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Ether Protecting Groups Revision

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Selective Anomeric Protection - Fischer Glycosylation: SN1 reaction: protonation of OH, loss of water, attack by alcohol. Attack by alcohol can occur from the top or bottom face of the oxonium ion so both
α- and β-anomers are produced. The reaction is reversible and so a thermodynamic mixture of anomeric isomers is formed: α: β 2:1
α-anomer preferred due to anomeric effect (axial rather than equatorial). Reaction is selective due to stability of the carbocation. Conditions:

• MeOH or BnOH

• HCl

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