- A NEW AND DIRECT ACCESS TO GLYCONO-1,4-LACTONES FROM GLYCOPYRANOSES BY REGIOSELECTIVE OXIDATION AND SUBSEQUENT RING RESTRICTION
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Treatment of partially protected or unprotected carbohydrates with the RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones by regioselective oxidation and subsequent ring restriction.
- Isaac, Isabelle,Stasik, Imane,Beaupere, Daniel,Uzan, Raoul
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p. 383 - 386
(2007/10/02)
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- 2-Acetamido-2-deoxyaldonolactones from sugar formazans
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A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.
- Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras
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- Aldonhydroximo-lactones. Preparation and Determination of Configuration
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The synthesis of the unprotected, (Z)-configurated hexon- and pentonhydroximo-lactones 2a-12a by oxidation of D-glucose, cellobiose, D-galactose, D-mannose, 2-acetamido-2-deoxy-D-glucose, D-ribose, and D-arabinose oxime with MnO2, Hg(OAc)2, or O2 in the p
- Beer, Dieter,Vasella, Andrea
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p. 2254 - 2274
(2007/10/02)
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