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- W2045017695 abstract "Abstract Treatment of methyl α- D -mannopyranoside (I) in succession in situ with p -toluenesulfonyl chloride, carbonyl chloride, and benzoyl chloride gave methyl 4- O -benzoyl-2,3- O -carbonyl-6- O-p -tolylsulfonyl-α- D -mannoside (III). Replacement of the p -tolylsulfonyloxyl group of III with iodide ion gave the 6-iodo derivative IV, which underwent reduction to give methyl 4- O -benzoyl-2,3- O -carbonyl-6-deoxy-α- D -mannoside (V). Replacement of the C-1 methoxyl group of V by bromide ion gave 4- O -benzoyl-2,3- O -carbonyl-6-deoxy-α- D -mannosyl bromide (VI), which underwent methanolysis by inversion, to yield methyl 4- O -benzoyl-2,3- O -carbonyl-6-deoxy-β- D -mannoside (VII). The bromide VI was coupled with digitoxigenin (VIII) to give, after saponification, 13% of 3-(β- D -rhamnopyranosyl)digitoxigenin (XI) and 48% of the corresponding α- D anomer X. Coupling of the bromide VI with strophanthidin (IX), followed by saponification, gave 6% of 3-(β- D -rhamnopyranosyl)strophanthidin (XIII) and 8% of the alternative anomeric form XII." @default.
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- W2045017695 date "1965-12-01" @default.
- W2045017695 modified "2023-09-23" @default.
- W2045017695 title "The partial synthesis of two 1,2-cis cardenolides" @default.
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- W2045017695 doi "https://doi.org/10.1016/s0008-6215(00)81757-7" @default.
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