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The specific reason for the high β-selectivity in the glycosylation of 43 in the absence of the C2-participatory group in 45 is unclear, although it is likely that this outcome is highly substrate dependent.
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33748500112
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note
-
The strategy of using 2,3-di-O-benzylidine-5-O-benzylapiofuranose instead of 76 as a the glycosyl donor for direct coupling with 52 was less attractive, given that such a donor required its preparation from 76 in a low-yielding sequence. Given that the conversion of 52 + 76 → → 77 is nearly quantitative over three steps, the alternate approach would have been considerably less efficient.
-
-
-
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49
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33748512464
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note
-
1H NMR, and MS data of synthetic S were identical to those of natural S, obtained by RP-HPLC of Quil A (Accurate Chemical & Scientific Corp.), a Quillaja extract known to contain traces of 5.
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