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0031000853
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For the synthesis of sialic acid C-pyranosides of sugars, see : Vlahov, I.R.; Vlahova, P.I.; Linhardt, R.J. J. Am. Chem. Soc. 1997, 119, 1480-1481.
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16
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84986694900
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For the preparation of C-glycosides of sialic acid derivatives, see e.g.: Paulsen, H.; Matschulat, P. Liebigs Ann. 1991, 487-495;
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Paulsen, H.1
Matschulat, P.2
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25
-
-
26844465903
-
-
note
-
Under the same conditions, the [4+3] adducts of 2-(methoxymethyloxy)furan, 2-[(tertbutyl)dimethylsilyloxymethyl]furan and methyl furan-2-carboxylate were obtained in 15%, 65% and 50% yield, the major adduct bearing the 2- and 4-bromo substituents in endo positions.
-
-
-
-
27
-
-
26844532497
-
-
note
-
2: C 44.7, H 3.75, Br 39.6; found: C 44.63, H 3.85, Br 39.55.
-
-
-
-
28
-
-
26844547439
-
-
note
-
2Si: C 48.75, 6.92, Br 24.95; found: C 48.65, H 6.84, Br 24.99.
-
-
-
-
30
-
-
26844443870
-
-
note
-
2Si: C 48.91, H 6.63, Br 25.03; found: C 48.64, H 6.54, Br 24.95.
-
-
-
-
31
-
-
84987553234
-
-
Le Drian, C.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161-168.
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Le Drian, C.1
Vionnet, J.-P.2
Vogel, P.3
-
32
-
-
26844583257
-
-
note
-
2: C 52.17, H 7.00; found: C 52.10, H 6.96.
-
-
-
-
34
-
-
9544223606
-
-
see also: Kleschick, W.A.; Buse, C.T.; Heathcock, C.H. J. Am. Chem. Soc. Ibid. 1977, 99, 247-248;
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Kleschick, W.A.1
Buse, C.T.2
Heathcock, C.H.3
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36
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33845561711
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Evans, D.A.; Vogel, E.; Nelson, J.V. J. Am. Chem. Soc. 1979, 101, 6120-6123;
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Nelson, J.V.3
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37
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0347195435
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Heathcock, C.H.; Buse, C.T.; Kleschick, W.A., Pirrung, M.C.; Sohn, J.E.; Rampe, J. J. Org. Chem. 1980, 45, 1066;
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Kleschick, W.A.3
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41
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0001523555
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Mann, J. Tetrahedron 1986, 42, 4611-4659.
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Mann, J.1
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42
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0030272259
-
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For the synthesis of other C-pyranosides following a similar approach, see: Lampe, T.F.J.; Hoffmann, H.M.R.; Bornscheuer, U.T. Tetrahedron Asym. 1996, 7, 2889-2900;
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Lampe, T.F.J.1
Hoffmann, H.M.R.2
Bornscheuer, U.T.3
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