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- W2023154037 abstract "Under anhydrous methanolysis conditions, methyl 2,3-O-isopropylidene-β-D-apio-D-furanoside (methyl 3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside, 4) can be prepared in high yield from 1,2-O-isopropylidene-α-D-apioL-furanose (1). The acetal migration was shown to be intramolecular; and the furanose ring opened and re-formed at the other primary hydroxyl during the reaction, thus inverting the configuration at C-3. Pfitzner-Moffatt oxidation of 4 gave an aldehyde, the stable oxime of which was shown to have the syn configuration. Starting from 1 and 4, the four possible methyl tri-O-methyl--D-apiosides were synthesized, and it was confirmed that apiose occurs with the D-furano configuration in apiin." @default.
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- W2023154037 date "1971-03-01" @default.
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- W2023154037 title "Apiose. III. A synthesis of methyl 2,3-O-isopropylidene-β-D-apio-D-furanoside involving intramolecular acetal migration, and stereospecific synthesis of apiose methyl ethers" @default.
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- W2023154037 doi "https://doi.org/10.1016/s0008-6215(00)81553-0" @default.
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