Diastereoisomeric Synthesis of Novel Analogues of d4T having an Isochroman Glycon Moiety

Christophe      Len

doi:10.2174/157017806774964422

Abstract

1,2-O-Isopropylidene-α-D-xylofuranose has been used as a chiral protecting group of the formyl group of 2-bromobenzaldehyde, in which it acts as a resolving agent leading to separable diastereoisomers when a new stereocenter is created by substitution of bromine by a 2,3-dihydroxypropyl chain. These separated diastereoisomers were cyclised to furnish the target nucleoside analogues of d4T as an isochroman.

Keywords: d4T, isochroman, D-xylose

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Letters in Organic Chemistry

Title: Diastereoisomeric Synthesis of Novel Analogues of d4T having an Isochroman Glycon Moiety

Volume: 3 Issue: 1

Author(s): Christophe Len

Affiliation:

Keywords: d4T, isochroman, D-xylose

Abstract: 1,2-O-Isopropylidene-α-D-xylofuranose has been used as a chiral protecting group of the formyl group of 2-bromobenzaldehyde, in which it acts as a resolving agent leading to separable diastereoisomers when a new stereocenter is created by substitution of bromine by a 2,3-dihydroxypropyl chain. These separated diastereoisomers were cyclised to furnish the target nucleoside analogues of d4T as an isochroman.

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Len Christophe, Diastereoisomeric Synthesis of Novel Analogues of d4T having an Isochroman Glycon Moiety, Letters in Organic Chemistry 2006; 3 (1) . https://dx.doi.org/10.2174/157017806774964422