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- W2069431330 startingPage "1492" @default.
- W2069431330 abstract "The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner. For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95% yield when a mixture of 3β and t-butylmagnesium bromide in benzene–ether was heated at about 75 °C to remove the ether; the reverse reaction (from 3α to (3β) did not proceed. The reaction of 3β with methylmagnesium iodide gave open-chain products (33%), besides 3α (30%). Twenty kinds of anomers were tested, and the mechanisms of the reactions were discussed. The cleavage of a benzyl- or trityl-protecting group with the Grignard reagent was also observed during the reaction." @default.
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- W2069431330 date "1981-05-01" @default.
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- W2069431330 title "The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings" @default.
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- W2069431330 doi "https://doi.org/10.1246/bcsj.54.1492" @default.
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