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0028815216
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The Ferrier reaction favors the obtention of α-anomer, chromatographically less polar than the corresponding 2β-anomer (Doboszewski, B.; Blaton, N.; Herdewijn, P. Tetrahedron Lett. 1995, 36, 1321-1324). Isopropanol has the advantage to give after hydrolysis the α-anomer as a solid directly purified by recrystallization (mp = 103 °C).
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24
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Sweeney, J.1
Perkins, G.2
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26
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0030184237
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Only N-1 nucleosides were observed without N-3 or O-alkylation by-products (Luyten, I.; Herdewijn, P. Tetrahedron 1996, 52, 9249-9262.)
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Luyten, I.1
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27
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0342912766
-
-
note
-
General procedure for the preparation of 9-15 : In a flask (100 mL) equipped with a magnetic stirrer and connected to a nitrogen atmosphere, a mixture of nucleobase (3 mmol) in dry acetonitrile (40 mL) was introduced. N, O-bis(trimethylsilyl) acetamide (BSA) (2.48 mL, 10 mmol) was added via a syringe and the suspension stirred at r.t. until complete dissolution. Pyran-3-one 1-3 (3 mmol) was added over 2 min followed by TMSOTf (1.3 mL, 7 mmol) via the syringe. The resulting solution was stirred for 2 h at R.T., then water (60 mL) was added. After concentration in vacuo, the aqueous solution was partitioned with EtOAc. After usual work-up, the residue consisted of crude 9-15.
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28
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0343347995
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note
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13C)-COSY spectra to establish the the relationship of H-atoms in compounds 23-27. No racemization at C-5′ occurs (Eu shift reagent, det. limit ca. 95 % e.e.).
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33
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0343783665
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0027932366
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Kakefuda, A.1
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35
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0001117585
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36
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0027222155
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Arango, J. H.; Geer, A.; Rodriguez, J.; Young, P. E.; Scheiner, P. Nucleosides Nucleotides 1993, 12, 773-784.
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Arango, J.H.1
Geer, A.2
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Young, P.E.4
Scheiner, P.5
-
37
-
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0343347994
-
-
note
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6 : C, 53.49; H, 7.05; N, 8.91%.
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