Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis of 7-Deoxy-D-glycero-D-gluco-heptose (SF-666 A)
Teiichiro ITO
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1975 年 39 巻 1 号 p. 273-275

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The synthesis of 7-deoxy-D-glycero-D-gluco-heptose (1) from 3, 5-O-benzylidene-1, 2-O-isopropylidene-α-D-glucofuranose (2) is described. Oxidation of compound (2) afforded 3, 5-O-benzylidene-1, 2-O-isopropylidene-α-D-gluco-hexodialdo-1, 4-furanose (3), which was then treated with methylmagnesium iodide to give 3, 5-O-benzylidene-1, 2-O-isopropylidene-7-deoxy-α-D-glycero-D-gluco-heptose (4) and its L-glycero-D-gluco isomer (5). Hydrolysis of (4) produced compound (1), which was identical with natural SF-666 A, a fermentation product of Streptomyces setonensis nov. sp.
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