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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 13
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Original Articles

A Novel Route to Pyrimidine Isodideoxynucleosides via Michael-Type Addition on Unsaturated Modified Sugars

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Pages 2325-2335 | Received 12 Dec 1996, Published online: 22 Aug 2006

References and Notes

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  • Among all the described procedures to oxidize compounds of type 1, this method (see, reference 15) is interesting when glycoside 6 is wanted, otherwise, way through hemiketal 2 (R = Me) gives more versatility for other nucleosides precursors.
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  • a) Reaction conditions have not been fully optimized; b) All yields are isolated yields; c) for data see experimental description.
  • It's well known that Michael addition is very sensitive to steric hindrance. As for NMR arguments used to determine stereochemistry, see Varela O. De fina G. de Lederkremer R. M. J. Chem Research (S) 1990 262 263 or Rizzo, C. J.; Dougherty, J. P.; Breslow, R., Tetrahedron Lett., 1992, 33, 4129–4132.
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  • As known, no racemization of C-5′ occurs in this step (see ref. 19). A single diastereoisomer was formed (Eu shift reagent, det. limit ca. 95% ee); see ref. 21.
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