Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Aminocyclitols. XXIX. Synthesis of Inosadiamines via 1,3-Biimino-1,3-dideoxy-inositols
Tetsuo SuamiSeiichiro OgawaHayashi UchinoMasaru Uchida
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1973 Volume 46 Issue 12 Pages 3840-3844

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Abstract

Hydrazinolysis of DL-1,4-dibromo-1,4-dideoxy-chiro-inositol (3a), followed by catalytic hydrogenation and acetylation, afforded di-N-acetyl-tetra-O-acetyl-neo-inosadiamine-1,3 (6a) and -scyllo-inosadiamine-1,3 (7) in 18% and 24% yields, respectively. From the intact hydrazinolyzate of 3a, two new stereoisomeric 1,3-biimino-1,3-dideoxy-inositols (4a and 5a) could be isolated, and their structures were established by correlating to the corresponding inosadiamines. A similar hydrazinolysis of 3,6-di-O-p-tolylsulfonyl-muco-inositol (12) gave sole crystalline 1,3-biimino compound (13a), whose structure was followed from its conversion into known di-N-acetyltetra-O-acetyl-myo-inosadiamine-4,6 (14). PMR spectra of four 1,3-biimino compounds were discussed.

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