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- W2062064620 abstract "The reaction of 2,3,4,6-tetra-O-benzyl-1-O-(p-nitrobenzoyl)-α-d-glucopyranose with (E)-penta-2,4-dienyltrimethylsilane and boron trifluoride etherate in acetonitrile afforded stereoselectively (E)-5-(tetra-O-benzyl-α-d-glucopyranosyl)-1,3-pentadiene (1) in good yield. The readily available penta-O-benzoyl-α-d-glucopyranose reacted with allyltrimethylsilane in the presence of boron trifluoride etherate in acetonitrile to give 3-(tetra-O-benzoyl-α-d-glucopyranosyl)-1-propene (2) and its β anomer (5) in yields of 60% and 2.3%, respectively. Diels-Alder cycloaddition of maleic anhydride to diene 1 afforded the adduct cis,cis-3-(tetra-O-benzyl-α-d-glucopyranosylmethyl)cyclohex- 4-ene-1,2-dicarboxylic anhydride (9) in high yield." @default.
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- W2062064620 date "1989-08-01" @default.
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- W2062064620 title "Preparative synthesis of C-(α-d-glucopyranosyl)-alkenes and -alkadienes: Diels-alder reaction" @default.
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- W2062064620 doi "https://doi.org/10.1016/0008-6215(89)85066-9" @default.
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