D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.
1992; Elsevier BV; Volume: 48; Issue: 43 Linguagem: Inglês
10.1016/s0040-4020(01)88323-x
ISSN1464-5416
AutoresNigel G. Cooke, D.A. Jones, Andrew Whiting,
Tópico(s)DNA and Nucleic Acid Chemistry
Resumo3,5-anhydro-1,2-O-isopropylidene-α-d-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.
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