Volume 21, Issue 37
Natural Products
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ChemInform Abstract: Design and Synthesis of New 1,4-Diaminocyclitol Aminoglycosides: Use of Maltose as the Key Starting Material.

N. SAKAIRI

N. SAKAIRI

Riken, Inst. Phys. Chem. Res., Wako, Saitama 351-01, Jap.

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M. HAYASHIDA

M. HAYASHIDA

Riken, Inst. Phys. Chem. Res., Wako, Saitama 351-01, Jap.

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A. AMANO

A. AMANO

Riken, Inst. Phys. Chem. Res., Wako, Saitama 351-01, Jap.

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H. KUZUHARA

H. KUZUHARA

Riken, Inst. Phys. Chem. Res., Wako, Saitama 351-01, Jap.

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First published: September 11, 1990

Abstract

Starting from the maltose derivative (I) the cyclitol glycosides (VII) and (VIII) are prepared in a multi-step synthesis.

ChemInform Abstract

Starting from the maltose derivative (I) the cyclitol glycosides (VII) and (VIII) are prepared in a multi-step synthesis. The transformation of the 1,6-anhydrohexopyranose moiety into a cyclitol moiety is accomplished by thiolysis of the anhydro ring under formation of a thioglycoside, e.g. (V), with subsequent Ferrier carbocyclisation to the cyclitol, e.g. (VI). The deoxy analogue of (VII), i.e. (VIII), is prepared analogously from (IV).

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