Abstract
Application of the oxo reaction to 1,2,4,6-tetra-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranose (1), followed by acetylation of the oxo products, gave crystalline 1,2,3′,4,6-penta-O-acetyl-3-deoxy-3-C-(hydroxymethyl)-α-D-glucopyranose (2) in about 30% yield. Conversion of 2 into the branched-chain sugar bromide, followed by condensation of the latter with 6-benzamidochloromercuripurine afforded a blocked branched-chain sugar nucleoside (5) in 67% yield based on 2. The nucleoside (5) was deblocked with methanolic sodium methoxide to afford 9-(3-deoxy-3-C-hydroxymethyl-β-D-glucopyranosyl)-adenine (6) in 75% yield.
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