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Simple approach to 1-O-protected (R)- and (S)-glycerols from l- and d-arabinose for glycerol nucleic acids (GNA) monomers research

✍ Scribed by Bogdan Doboszewski; Piet Herdewijn

Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 216 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2011.05.073

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✦ Synopsis

5-O-Protected (-Tr, -Sitert-BuPh 2 ) D-and L-arabinofuranoses easily available in multigram quantities were converted to (S)-and (R)-1-O-protected glycerols, respectively, via oxidation (NaIO 4 ) and reduction (NaBH 4 ). Sources of chirality in the targets are the C4 atoms in the substrates. This stereospecific procedure permits a very simple access to both enantiomeric 1-O-protected glycerols for GNA monomers work.