Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group

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Abstract

1,2-O-Isopropylidene-α-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. © 2001 Published by Elsevier Science Ltd.

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Ewing, D. F., Len, C., Mackenzie, G., Ronco, G., & Villa, P. (2000). Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group. Tetrahedron Asymmetry, 11(24), 4995–5002. https://doi.org/10.1016/S0957-4166(00)00488-2

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