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Can I read Reaction of Butyllithium with Benzylidene Acetals of Aldopyranosides and 1,5-Anhydroalditols on EtoBox?
Reaction of Butyllithium with Benzylidene Acetals of Aldopyranosides and 1,5-Anhydroalditols by Derek Horton; Wolfgang Weckerle is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
What is Reaction of Butyllithium with Benzylidene Acetals of Aldopyranosides and 1,5-Anhydroalditols about?
Under suitable conditions, butyllithium selectively cleaves 5-membered benzylidene acetals (1,3-dioxolane ring) leaving the 6-membered analogs (1,3dioxane ring) intact in aldopyranoside and 1,5-anhydroalditol derivatives. The usual course of the reaction involves expulsion of the elements of benzaldehyde to give an enolate anion and thence a vicinal deoxyketone. The reaction is strongly regioselective and may be interpreted as proceeding via abstraction of the quasiaxial hydrogen atom on the sugar ring that is also part of the 1,3-dioxolane ring. Controlled routes of considerable synthetic utility are thereby feasible. In certain situations, an alternative reaction-pathway prevails that involves expulsion of the elements of benzoate anion with the formation of an alkene, the corresponding ring-unsaturated pyranose derivative.
Who reads Reaction of Butyllithium with Benzylidene Acetals of Aldopyranosides and 1,5-Anhydroalditols?
It is typically read by researchers, students, and practitioners in Biochemistry, Genetics and Molecular Biology.
- Author
- Derek Horton; Wolfgang Weckerle
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)
- Published
- 1988
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)