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Synlett 1995; 1995(2): 167-168
DOI: 10.1055/s-1995-4892
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Regioselective Ring Opening of Glucose Derived Spiro Epoxides

Luigi Lay, Francesco Nicotra, Luigi Panza* , Giovanni Russo
  • *Dipartimento di Chimica Organica e Industriale, Centro per lo Studio delle Sostanze Organiche Naturali del CNR, via Venezian 21, 20133 Milano, Italy
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Publication Date:
31 December 2000 (online)

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Spiro epoxides 2 derived from glucose can be opened either in acidic or basic conditions with opposite regioselectivity. Some examples with different nucleophiles are described. The procedure give access to intermediates which can be used in glycosidation reactions or in the synthesis of modified ketosugars.

Exo-glycal - epoxides - dimethyldioxirane - regioselective ring opening