Acid- mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

• Katsunori Tanaka and
• Koichi Fukase

Beilstein J. Org. Chem. 2009, 5, No. 40, doi:10.3762/bjoc.5.40

• conditions enabled the preparation of key synthetic intermediates for oligosaccharides on a multi-gram scale, eventually leading to a total synthesis of the asparagine-linked oligosaccharide (N-glycan) [32]. A significant improvement has also been achieved for dehydration, which resulted in the industrial

• of mammalian N-glycans of the diverse structures, have motivated us to establish a practical and library-directed synthesis of the complex-type N-glycans on solid-support [32]; the initial target of our strategy is a sialic acid-containing N-glycan with asymmetric branching chains (Figure 1), which

• is difficult to obtain from natural sources. To prepare the target N-glycan as well as other diverse structures of this family in an efficient manner, we designed fragments a–d with N-phenyltrifluoroacetimidate as the leaving group, which can be efficiently glycosylated on solid-support to construct