1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuran ose, a convenient precursor for the stereospecific synthesis of nucleoside analogues with the unnatural beta-L-configuration.
The title compound 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose (5), a useful precursor for the stereospecific synthesis of beta-L-nucleoside analogues as potential antiviral agents, has been synthesised by a multi-step reaction sequence from L-xylose with a 38% overall yield. The preparation involved conversion of L-xylose to 1,2-O-isopropylidene-alpha-L-xylofuranose which, upon selective 5-O-benzoylation and subsequent radical deoxygenation, provided the protected 3-deoxy sugar derivative. Finally, cleavage of the acetonide group gave the resulting 5-O-benzoyl-3-deoxy-L-erythro-pentose which was acetylated to afford crystalline alpha,beta-5.
Mathé
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Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR CNRS-UM II 5625, Université Montpellier II, France. cmathe@univ-montp2.fr
Imbach
J L
JL
Gosselin
G
G
D000089:Acetic Anhydrides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis*; D010429:Pentoses / Q000138:chemical synthesis*
C410155:1,2-di-O-acetyl-5-O-benzoyl-3-deoxypentofuranose; D000089:Acetic Anhydrides; D006027:Glycosides; D009705:Nucleosides; D010429:Pentoses; C031800:acetic anhydride