A novel method for constructing β-D-mannosidic, 2-acetamido-2-deoxy-β-D-mannosidic and 2-deoxy-D-arabino-hexopyranosidic units from the bis(triflate) derivative of β-D-galactoside

Article abstract of DOI:10.1246/bcsj.70.885

An efficient construction of the β-D-mannosidic, 2-acetamido-2-deoxy-β-D-mannosidic, 2-deoxy-2-fluoro-β-D-mannosidic, and 2-deoxy-β-D-arabino-hexopyranosidic units from the same intermediate, 2-4-bis(O-trifluoromethylsulfonyl) derivative of β-D-galactoside, was achieved in good yields in a stepwise inversion at C-4 and C-2 by using cesium acetate, n-Bu₄NN₃, n-Bu₄NF, and n-Bu₄NBH₄. A convenient and practical protection of β-D-mannoside to the straightforward synthesis of antennary oligosaccharides was also achieved by using cesium trifluoroacetate.