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Compounds 1-3 were prepared according to a modified literature procedure starting from D-galactose for detailed synthesis and characterization see ref 15a and Supporting Information, Peracetylation of D-galactose followed by transformation of the anomeric acetyl into benzyl ether, deacetylation, TBDPS protection of the primary hydroxyl group, introduction of the 3,4-O-acetal and ester protection of 2-OH and the subsequent silyl ether deprotection by TBAF and isopropylidene removal using Dowex H+ provided the corresponding model compounds 1-3 in approximately 40% overall yields over eight steps
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+ provided the corresponding model compounds 1-3 in approximately 40% overall yields over eight steps.
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1H NMR spectra for all of the synthesized and purified compounds were analyzed with PERCH NMR software for complete spectral analyses, see: Laatikainen, R.; Niemitz, M.; Weber, U.; Sundelin, J.; Hassinen, T.; Vepsäläinen, J. J. Magn. Reson. Ser. A 1996, 120, 1-10. The acyl group migration was followed with Varian 500 and 600 MHz (equipped with a cold probe) Inova Spectrometers and the migration products assigned by standard 2D NMR techniques.
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1H NMR spectra for all of the synthesized and purified compounds were analyzed with PERCH NMR software for complete spectral analyses, see: Laatikainen, R.; Niemitz, M.; Weber, U.; Sundelin, J.; Hassinen, T.; Vepsäläinen, J. J. Magn. Reson. Ser. A 1996, 120, 1-10. The acyl group migration was followed with Varian 500 and 600 MHz (equipped with a cold probe) Inova Spectrometers and the migration products assigned by standard 2D NMR techniques.
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