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Aminocyclitols. XI. Studies on the Synthesis of muco -Inosadiamines and Inosatetraamine

1967; Oxford University Press; Volume: 40; Issue: 6 Linguagem: Inglês

10.1246/bcsj.40.1488

1348-0634

Tetsuo Suami, Frieder W. Lichtenthaler, Seiichiro Ogawa,

Carbohydrate Chemistry and Synthesis

Abstract muco-lnositol was synthesized from 1, 4, 5, 6-tetra-O-acetyl-3-O-sulfonyl-myo-inositol in a fairly good yield by a new synthetic route. When sulfonyloxy groups were replaced by azide ion in muco-inositol derivatives, muco-inosadiamine-3, 6, myo-4, 6 and muco-inosatetraamine-1, 2, 4, 5 were obtained. Their structures were established by means of proton magnetic resonance spectro-scopy. By an analogous reaction, 2, 4, 5, 6-tetra-O-acetyl-1, 3-di-O-p-toluenesulfonyl-myo-inositol gave muco-inosadiamine-1, 4.