- Highly stereoselective α-sialylation. Synthesis of GM3-saccharide and a bis-sialic acid unit
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The novel sialyl donor methyl [ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)-2,3,5-trideox y-D-erythro-α-L-gluco-2-nonulopyranosid]onate (6) was synthesized in six steps from N-acetylneuraminic acid in an overall yield of 47%. Donor 6 was shown to be superior to conventional sialyl donors in that the sialylation yields were higher, even with sterically hindered and unreactive sialyl acceptors, and the α/β-selectivity was virtually complete.
- Ercegovic,Magnusson
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p. 3378 - 3384
(2007/10/02)
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- A New N-Acetylneuraminic Acid Donor for Highly Stereoselective α-Sialylation
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The new sialyl donor 6 (prepared from N-acetylneuraminic acid in 44percent yield over six steps) effects clean α-sialylation of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexabenzyl-β-D-lactoside in 67percent yield.
- Ercegovic, Teddy,Magnusson, Goeran
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p. 831 - 832
(2007/10/02)
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