Hiroki Shimizu, Yukishige Ito, Yuji Matsuzaki
Jan 23, 1996
Citations
0
Influential Citations
23
Citations
Journal
Bioscience, biotechnology, and biochemistry
Abstract
Phthaloyl (Phth) is a valuable amino-protecting group for use in synthetic carbohydrate chemistry. Its strong 1,2-trans-directing nature in a glycosylation reaction, when it is introduced to the C-2 position of a glycosyl donor, makes the construction of beta-GlcNAc or beta-GalNAc glycosides quite straightforward. The Phth group can be removed by using an appropriate nucleophile, most typically hydrazine; however, this transformation often requires a long reaction time at elevated temperature when applied to a large oligosaccharide. We studied the 4,5-dichlorophthaloyl (DCPhth) group as an alternative to Phth. A thioglycoside carrying a DCPhth group at the C-2 position was reacted with alcohol by the action of PhSeNPhth-TMSOTf to selectively give the corresponding beta-glycoside. DCPhth could then be removed under mild conditions by using ethylenediamine or hydrazine/MeOH at room temperature.