Glycosyl 6-Nitro-2-benzothiazoate. A Highly Efficient Donor for β-Stereoselective Glycosylation
- 13 March 2003
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 32 (4) , 340-341
- https://doi.org/10.1246/cl.2003.340
Abstract
Highly β-stereoselective glycosylations of glycosyl acceptors having a primary hydroxyl group by using a novel glycosyl donor, α-glycosyl 6-nitro-2-benzothiazoate (3), proceeded smoothly in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) in CH2Cl2 at −78 °C to afford the corresponding glycosides in high yields. The donor 3 gave β-saccharides more dominantly compared with those using other α-glycosyl donors such as thioform- and trichloroacet-imidates or fluoride under the same conditions.Keywords
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