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- W4205657070 abstract "Abstract A pyranose ring contraction of 2,3-di-O-silylated O-galactopyranosides with retention of aglycone promoted by anhydrous trifluoroacetic acid (TFA) in CH2Cl2 was demonstrated for the first time. In addition, TFA-promoted pyranose ring contraction of 2,3-bis-O-(triisopropylsilyl)-d-galactopyranose with formation of the corresponding anomeric triols in furanose form was successfully performed. A representative series of β-d-galactopyranosides with Me, Bn, allyl, or 3-(trifluoroacetamido)propyl aglycones has been investigated. TBDPS protective groups were found to be more stable than TIPS groups under conditions of TFA-promoted pyranose ring contraction. An easy access to 2,3-di-O-TBDPS-substituted allyl and benzyl galactofuranosides and 2,3-bis-O-(triisopropylsilyl)-β-d-galactofuranose may present an advantage in synthesis of selectively protected monosacharide building blocks, useful for the synthesis of biologically important oligosaccharides." @default.
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- W4205657070 date "2022-01-04" @default.
- W4205657070 modified "2023-10-11" @default.
- W4205657070 title "Trifluoroacetic Acid Promoted Ring Contraction in 2,3-Di-O-silylated O-Galactopyranosides and Hemiacetals" @default.
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- W4205657070 doi "https://doi.org/10.1055/a-1730-9458" @default.
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