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Facile Separation of Chiral 1,3-Dihydrobenzo[ C ]Furan Derivatives Using a D -Xylose Moiety as a Protecting Group by David F. Ewing; Christophe Len; Grahame Mackenzie; Gino Ronco; Pierre Villa is a Chemistry article available to read on EtoBox.

What is Facile Separation of Chiral 1,3-Dihydrobenzo[ C ]Furan Derivatives Using a D -Xylose Moiety as a Protecting Group about?

1,2-O-Isopropylidene-a-D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues.

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Author

David F. Ewing; Christophe Len; Grahame Mackenzie; Gino Ronco; Pierre Villa

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)