Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate

Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate

A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert...

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Veröffentlicht in:Tetrahedron letters 2013-07, Vol.54 (29), p.3831-3833
Hauptverfasser: Cui, Yanli, Cheng, Zhaodong, Mao, Jianwei, Yu, Yongping
Format: Artikel
Sprache:eng
Schlagworte:
Acetylation
Ammonium acetate
Carbohydrates
Desilylation
Glycosides
Inert
Methodology
Protecting groups
Regioselectivity
Sugars
Tetrahedrons
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Beschreibung
Zusammenfassung:A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.05.039