Journal
TETRAHEDRON LETTERS
Volume 55, Issue 11, Pages 1920-1923Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.01.151
Keywords
Selenoglycoside; Selenoacetal; Transacetalization; Carbohydrate mimetics
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Funding
- World Premier International Research Center Initiative (WPI), MEXT, Japan
- MEXT of Japan [22380067, 23688014, 24110505]
- Grants-in-Aid for Scientific Research [23688014, 24110505, 22380067] Funding Source: KAKEN
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A facile reaction for constructing selenoglycosides has been developed based on the transacetalization reaction between a selenoacetal and a glycosyl imidate. Glycosyl imidates were activated with TMSOTf to produce oxocarbenium ion, which reacted with benzyloxymethyl alkyl (aryl) selenide, providing alky (or aryl) selenoglycosides in high yields. Furthermore, this reaction was utilized in the synthesis of 2-(trimethylsilyl)ethylselenoglycoside, which, upon treatment with TBAF in the presence of an electrophile, was transformed into other selenoglycosides. (c) 2014 Elsevier Ltd. All rights reserved.
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