An improved and general synthesis of N-glycosylated oxindoles by SET-reduction of isatin-N-glycosides

Oxindole- N -glycosides were efficiently prepared by reduction of acetyl- and formyl protected isatin- N -glycosides with low-valent titanium and following cleavage of the protecting groups under basic conditions. The products could be isolated as pure anomers – no noticeable anomerization took place. • A variety of oxindole- N -glycosides were efficiently prepared from readily available starting materials. • The products were isolated as pure anomers. • Products could be deprotected and are not readily available by other methods.

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Publication Details

Journal
Tetrahedron Letters
Published
2026-02-12
DOI
https://doi.org/10.1016/j.tetlet.2026.156004
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.00
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article

An improved and general synthesis of N-glycosylated oxindoles by SET-reduction of isatin-N-glycosides

Dirk Michalik, Martin Hein, Peter Ehlers, Anna Frey
Tetrahedron Letters
Carbohydrate Chemistry and Synthesis
article

An improved and general synthesis of N-glycosylated oxindoles by SET-reduction of isatin-N-glycosides

Dirk Michalik, Martin Hein, Peter Ehlers, Anna Frey
article en

Abstract

Oxindole- N -glycosides were efficiently prepared by reduction of acetyl- and formyl protected isatin- N -glycosides with low-valent titanium and following cleavage of the protecting groups under basic conditions. The products could be isolated as pure anomers – no noticeable anomerization took place. • A variety of oxindole- N -glycosides were efficiently prepared from readily available starting materials. • The products were isolated as pure anomers. • Products could be deprotected and are not readily available by other methods.

Tetrahedron LettersVol. 178
Leibniz Institute for Catalysis (DE), University of Rostock (DE)
Openalex Percentile: Top 57%
Carbohydrate Chemistry and Synthesis
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