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- Title
Ring Cleavage Reactions of Methyl α-D-Allopyranoside Derivatives with Phenylboron Dichloride and Triethylsilane.
- Authors
Kojima, Masaru; Nakamura, Yutaka; Ito, Yuusuke; Takeuchi, Seiji
- Abstract
In the course of our studies on the regioselective carbon-oxygen bond cleavage of the benzylidene acetal group of hexopyranosides with a reducing agent, we found that a combination of a Lewis acid and a reducing agent triggered a ring-opening reaction of the pyranose ring of methyl α-D-allopyranosides. The formation of an acyclic boronate ester by the attachment of a hydride ion at C-1 indicated that the unexpected endocyclic cleavage of the bond between the anomeric carbon atom and the pyranose ring oxygen atom proceeded via an oxacarbenium ion intermediate produced by the chelation between O5/O6 of the pyranoside and the Lewis acid, followed by nucleophile substitution with a hydride ion at C1.
- Subjects
ANALYTICAL chemistry; CHEMICAL reactions; CHEMICAL structure; ORGANIC compounds; RING-opening polymerization; LEWIS acids
- Publication
Molecules, 2011, Vol 16, Issue 12, p10303
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules161210303