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37.7.1.1.3.2.2 Method 2: Deamination of 1-Amino-1-deoxypentitols

DOI: 10.1055/sos-SD-037-00438

Robina, I.; Vogel, P.Science of Synthesis, (200837656.

1-Amino-1-deoxypentitols (e.g., 57), prepared from the corresponding oximes (e.g., 56) by hydrogenation over platinum, react with nitrous acid at 0°C to give the corresponding 1,4-anhydropentitols (e.g., 58) that have the same configuration as the starting materials. The deamination reactions differ from the acid treatments in that they take place at lower temperatures. They are influenced by the conformation of the starting compounds and are not reversible. The amount of 1,4-anhydropentitol formed decreases through the series xylo > ribo=arabino >> lyxo. Small amounts of 2,5-anhydrido derivatives are formed by ring closure with inversion of configuration at C2.[‌58‌]

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