874904-99-1Relevant academic research and scientific papers
Renaissance of traditional organic reactions under microfluidic conditions: A new paradigm for natural products synthesis
Tanaka, Katsunori,Fukase, Koichi
experimental part, p. 983 - 990 (2010/04/22)
Continuous flow synthesis for bioactive natural products is described. Efficient procedures using the microfluidic system were developed for the large-scale synthesis of important synthetic units of asparagine-linked oligosaccharide in glycoprotein. Advantageous aspects of microfluidic conditions, i.e., efficient mixing, fast heat transfer, and residence time control led to cation-mediated reactions, such as a-sialylation, β-mannosylation, and reductive opening of the benzylidene acetal groups in high yields. Microfluidic dehydration was developed for the industrial-scale synthesis of the immunostimulating natural terpenoid, pristane. The base-mediated aldol condensation in an aqueous biphasic system enabled the multigram synthesis of β-hydroxyketones in high yields. 2009 American Chemical Society.
Highly efficient α-sialylation by virtue of fixed dipole effects of N-phthalyl group: Application to continuous flow synthesis of α(2-3)-and α(2-6)-Neu5Ac-Gal motifs by microreactor
Tanaka, Shin-Ichi,Goi, Takashi,Tanaka, Katsunori,Fukase, Koichi
, p. 369 - 394 (2008/04/12)
Highly α-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 α-selectivity. The microfluidic system was applied to the present α-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. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.
