Studies on Nitro Sugars. III. The Synthesis of 3-Nitrohexofuranose Derivatives

The oxidation of l,2;5,6-di-O-isopropylidene-3-oximino-α-D-ribo-hexofuranose (1) with trifluoroperacetic acid at a low temperature afforded, in a 75% yield, the corresponding 3-nitro-allofuranose (3), but at a high temperature it gave at least three nitro compounds, i.e., 3, 3-deoxy-1,2-O-isopropyli...

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Published inBulletin of the Chemical Society of Japan Vol. 46; no. 5; pp. 1532 - 1535
Main Authors Takamoto, Tetsuyoshi, Yokota, Yoh-ichi, Sudoh, Rokuro, Nakagawa, Toshio
Format Journal Article
LanguageEnglish
Published The Chemical Society of Japan 01.05.1973
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Summary:The oxidation of l,2;5,6-di-O-isopropylidene-3-oximino-α-D-ribo-hexofuranose (1) with trifluoroperacetic acid at a low temperature afforded, in a 75% yield, the corresponding 3-nitro-allofuranose (3), but at a high temperature it gave at least three nitro compounds, i.e., 3, 3-deoxy-1,2-O-isopropylidene-3-nitro-α-D-allofuranose (6) and 3,6-anhydro-3-nitro-α-D-glucofuranose (8). 6 was converted to 5,6-di-O-acetate (7) and confirmed by comparison with the 3-epimer (11), which was prepared by the acetonation of 3-deoxy-3-nitro-D-glucose, partial hydrolysis and acetylation. The structure of 8 was instrumentally determined and supported by the fragmentation pathways in its mass spectrometry. The formation of 8 was assumed to proceed through nitronic acid (5) as an intermediate.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.46.1532