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Table 3 ;6-Mannoside Formation from Thioglycosides with PhSOTf in CH2Cl2

Glycosyl donor

Glycosyl acceptor

Product and yield (%)

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our ^-mannosylation protocol, with the expectation that even higher ^-selectivity would be observed. This proved to be the case with a range of primary, secondary, and tertiary thiols (Table 4) with no a-thiomannoside being detected in any case. The yields, although good, were nevertheless somewhat less than we had typically observed with alcohols [38]. We attribute this phenomenon to the partial capture of the soft nucleophiles by one or other of the several sulfur-based electrophilic byproducts present in the reaction mixture.

Table 3 Continued

Glycosyl donor

Glycosyl acceptor

Product and yield (%)

0 0

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