Spacer-mediated synthesis of bis-spiroketal disaccharides: Nonsymmetrical furanose-pyranose difructose dianhydrides
The stereochemical outcome of the dimerization reaction of D-fructose, leading to tricyclic bis-spiroketal systems, can be tuned by inserting a xylylene template between the reacting moieties. Spirocyclization becomes then an intramolecular process, the available conformational space depending on th...
| Authors: | , , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2007 |
| Country: | España |
| Institution: | Universidad de Sevilla (US) |
| Repository: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:idus.us.es:11441/70295 |
| Online Access: | https://hdl.handle.net/11441/70295 https://doi.org/10.1055/s-2007-991055 |
| Access Level: | Open access |
| Keyword: | Acetals Difructose dianhydrides Oligosaccharides Spiro compounds Spiroacetals |
| Summary: | The stereochemical outcome of the dimerization reaction of D-fructose, leading to tricyclic bis-spiroketal systems, can be tuned by inserting a xylylene template between the reacting moieties. Spirocyclization becomes then an intramolecular process, the available conformational space depending on the nature of the tether. The methodology is here illustrated by the stereoselective synthesis of two nonsymmetrical di-D-fructose dianhydrides present in commercial caramel |
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