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Synthesis 2001(5): 0751-0754
DOI: 10.1055/s-2001-12773
PAPER
© Georg Thieme Verlag Stuttgart · New York

Facile and Efficient Synthesis of ido-Heptulosan via a Strategy Derived from Mo(VI)-Catalysed Reactions

Zuzana Hricovíniová
Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava, Slovakia
Fax: +421(7)5941-0222; e-Mail: chemhric@savba.sk;
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Publikationsverlauf

Received 4 January 2001
Publikationsdatum:
15. Oktober 2004 (online)

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Abstract

A simple and high-yielding method for the preparation of 2,7-anhydro-β-d - ido-heptulopyranose (IDO) is described. It utilises the ability of molybdate ions to create the conditions for the skeletal rearrangement in the molecule of 2-C-branched aldose. This evidence is used in the synthesis of IDO from 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-d-gulofuranose in one step. The title compound is obtained in 95% yield.

Key words

ido-heptulosan - 2,7-anhydro-β-d - ido-heptulopyranose - 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-d-gulofuranose - 2-C-(hydroxymethyl)-d -gulose - Mo(VI) catalysis

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Hricovíniová, Z.; Hricovíni, M.; Petru, L.; Monatsh. Chem. in press.