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note
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Preliminary results indicated that NIS/TfOH-mediated glycosylation of 1,2-di-O-tert-butyldiphenylsilyl-sn-glycerol with ethyl 1-thio-α/β-D-glucopyranosyl donor 7 gave an inseparable mixture of the required product and an α-linked dimeric byproduct (15-20%). The formation of this byproduct may be explained by acid-catalyzed migration of a silyl protective group.
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0343217035
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note
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In this respect, it is of interest to note that methylthiomethylation of 20 in a mixture of acetic acid/acetic anhydride/dimethyl sulfoxide gave a much lower yield (30%) in comparison with the dimethyl sulfide/BPO-mediated reaction (63%).
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28
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0000800544
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