- Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides
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The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-oxy>methyl>-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15percent yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-α- and -β-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside.Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes.Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.
- Rehnberg, Nicola,Magnusson, Goeran
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p. 5467 - 5476
(2007/10/02)
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- Novel One-Pot Synthesis of a New Class of Compounds Involving Coupling of Sugars and Amino Acids via Triflates.
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A new class of pharmacologically interesting compounds has been synthesized by way of a novel C-N coupling reaction between partially blocked sugars and a variety of suitably protected naturally occuring amino acids.The free amino functions of the latter
- Kowollik, W.,Malik, A.,Afza, N.,Voelter, W.
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p. 3325 - 3330
(2007/10/02)
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