期刊
JOURNAL OF CARBOHYDRATE CHEMISTRY
卷 26, 期 7-9, 页码 369-394出版社
TAYLOR & FRANCIS INC
DOI: 10.1080/07328300701634796
关键词
alpha-sialylation; n-phthalyl group; fixed dipole effects; microreactor; oligosaccharides
Highly alpha-selective sialylation of sialic acid N-phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The fixed dipole effect of the N-phthalyl group was proposed to explain the high reactivity and a-selectivity. The microfluidic system was applied to the present alpha-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides. [GRAPHICS]
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