The Journal of Organic Chemistry

Chiral aldehydes by ring contraction of pento-and hexopyranoside epoxides

N Rehnberg, G Magnusson

文献索引：Rehnberg, Nicola; Magnusson, Goeran Journal of Organic Chemistry, 1990 , vol. 55, # 20 p. 5467 - 5476

被引用次数: 25

摘要

The chiral aldehydes (-)-(2S, 5S)-and (-)-(2S, 5R)-2-[[[dimethyl (1, 1, 2-trimethylpropyl) silyl] oxy] methyl]-5-methoxy-2, 5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-0-silylated methyl 2, 3-and 3, 4-anhydro-a-and-PD-hexopyranosides, obtained in two steps from methyl a-and P-Dglucopyranoside. Rearrangement of various other pento-and hexoside ...

~99%

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