Journal of Carbohydrate Chemistry p. 417 - 434 (2004)
Update date:2022-08-05
Topics:
Liberek, Beata
Dabrowska, Aleksandra
Frankowski, Ryszard
Smiatacz, Zygfryd
Methyl 3-azido-2,3-dideoxy-α/β-D-arabino- and -α/β-D-ribo-hexopyranosides were transformed into 6-iodo analogues via p-tolylsulfonyl compounds. Elimination of hydrogen iodide from 6-iodo glycosides provided methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-α- and -β-D-threo-hex-5-eno-pyranosides or 3-azido-4-O-p-tolylsulfonyl-2,3,6- trideoxy-α-D-threo- and -β-D-erythro-hex-5-eno-pyranosides. Ferrier's carbocyclization of 4-O-acetyl-3-azido-2,3,6-trideoxy-α- and -β-D-threo-hex-5-eno-pyranosides gave (2S,3R,5R)-2-acetoxy-3-azido-5- hydroxycyclohexanone, which was converted into oxime. The 2-OAc group in oxime was substituted by azide ion to yield (2R,3R,5R)-2,3-diazido-5- hydroxycyclohexanone oxime. The configuration and conformation of all products are widely discussed on the basis of the 1 H and 13 C NMR. Copyright
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