The Four-Carbon Elongation of Aldehydo Sugars Using 2-(Trimethylsiloxy)furan: A Butenolide Route to Higher Monosaccharides

DOI: 10.1021/jo00296a001

Source and publish data:

Journal of Organic Chemistry p. 2565 - 2567 (1990)

Update date:2022-08-05

Topics:

Authors:

Casiraghi, Giovanni

Colombo, Lino

Rassu, Gloria

Spanu, Pietro

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Article abstract of DOI:10.1021/jo00296a001

2-(Trimethylsiloxy)furan is an available nucleophilic four-carbon synthon that reacts with sugar aldehydes and imines in the presence of BF3 etherate, furnishing γ-C-glycosylated butenolides with very high diastereoselection.The title butenolides represent versatile homochiral candidates to be manipulated into higher carbon sugars.

Full text of DOI:10.1021/jo00296a001

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