This paper describes a new route for the synthesis of N-(1'-homo-L-gulitol)nucleosides I (B = Ura, Thy, or Ade) and amino sugar analogs of N-(1'-homo-L-glucitol)nucleosides II (R = OPh, OH, Ade) by nucleophilic epoxide ring-opening followed by O-heterocyclization of 1,2:5,6-dianhydro-3,4-di-O-benzyl-D-mannitol and 1,2:5,6-dianhydro-3,4-diazido-D-iditol, resp. Magnesium perchlorate [Mg(ClO4)2] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymine and adenine, with these bis(epoxides).

Synthesis of 1'-homo-N-nucleosides from hexitols / Saladino, R., Ciambecchini, U., Hanessian, S.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 22:(2003), pp. 4401-4405.

Synthesis of 1'-homo-N-nucleosides from hexitols

SALADINO R;
2003

Abstract

This paper describes a new route for the synthesis of N-(1'-homo-L-gulitol)nucleosides I (B = Ura, Thy, or Ade) and amino sugar analogs of N-(1'-homo-L-glucitol)nucleosides II (R = OPh, OH, Ade) by nucleophilic epoxide ring-opening followed by O-heterocyclization of 1,2:5,6-dianhydro-3,4-di-O-benzyl-D-mannitol and 1,2:5,6-dianhydro-3,4-diazido-D-iditol, resp. Magnesium perchlorate [Mg(ClO4)2] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymine and adenine, with these bis(epoxides).
2003
1'-homo-N-nucleosides; synthesis; sugars
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of 1'-homo-N-nucleosides from hexitols / Saladino, R., Ciambecchini, U., Hanessian, S.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 22:(2003), pp. 4401-4405.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1766480
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