Issue 26, 2025

Elucidation of the acid reactivity of polyhedral orthoformates for the synthesis of carbasugar derivatives

Abstract

Carbasugar-containing natural products such as uvaridacol L have a variety of bioactivities, motivating chemists to develop methods for their synthesis. The conversion of myo-inositol is one of the most efficient methods for the synthesis of carbasugars. However, selective conversion of myo-inositol derivatives remains to be explored. In our synthesis of uvaridacol L derivatives, we found that the methoxy olefin derivatives of orthoester-protected myo-inositols, the key synthetic intermediates of our study, exhibit differing reaction selectivities depending on their geometric isomerism and substituents. Here we present new insights that contribute to the synthesis of carbasugar-type derivatives by elucidating the mechanism of the selectivity using density functional theory (DFT) calculations.

Graphical abstract: Elucidation of the acid reactivity of polyhedral orthoformates for the synthesis of carbasugar derivatives

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Article information

Article type
Paper
Submitted
12 Feb 2025
Accepted
08 May 2025
First published
19 Jun 2025
This article is Open Access
Creative Commons BY license

RSC Adv., 2025,15, 20734-20744

Elucidation of the acid reactivity of polyhedral orthoformates for the synthesis of carbasugar derivatives

K. Usuguchi, A. Takagi, I. Takashima and K. Okuda, RSC Adv., 2025, 15, 20734 DOI: 10.1039/D5RA01049G

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