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Inne
Synthesis and chemical transformation of 2-acetoxyimino-3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl azide.
Autorzy
Rok wydania
1993
Czasopismo
Journal of Carbohydrate Chemistry
Numer woluminu
12
Strony
1161-1171
DOI
10.1080/07328309308020125
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The title compound 3 has been synthesized from 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride (1) via compound 2. Azide reduction of 3 is accompanied by O→N-acetyl migration to afford N-acetyl-N-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-β-D-arabino-hexopyranosyl) amine (4), also characterized as its Z and E peracetates. On the basis of IR, 1H NMR and X-ray structural data from compound 4, its β-NHAc configuration, (Z) 2-hydroxyimino, and °S2 conformation, were established.
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