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-1 by direct lithiation of commercially available polystyrene resin (crosslinked with 1% divinylbenzene, 100-200 mesh) with nBuLi and subsequent treatment with dichlorodiisopropylsilane (see also ref. [12]).
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27
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12244250911
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note
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This enables the direct analysis of diastereomeric N-galactosylated products and of potential side products and facilitates the analysis of complex reaction sequences on the solid-phase.
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The presence of the pivaloyl group at C-2 is necessary for effective diastereofacial differentiation of glycosyl imines (review: K. Rück, H. Kunz, Angew. Chem. 1993, 105, 355-377; Angew. Chem. Int. Ed. Engl. 1993, 32, 336-358); the other hydroxy functions are pivaloyl or pseudopivaloyl (as at C-6 in 4) protected, to increase the stability of the auxiliary against organometallic reagents.
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37
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12244296597
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note
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The loading capacity was calculated from the nitrogen content of a resin sample that was washed thoroughly and dried for 48 h at 40 °C under high vacuum.
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39
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12244299073
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After evaporation of the combined cleavage and washing solutions, the residue was subjected to filtration through a short plug of silica, the crude product was eluted with petroleum ether/ ethyl acetate (1/1), and after removal of the solvent the residue was analyzed by HPLC-MS.
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