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Expedient synthesis of an α-S-(1→6)-linked pentaglucosyl thiol
1College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
Abstract:
An α-S-(1→6)-linked pentaglucosyl thiol has been synthesized in a convenient and stereoselective way. Key steps of the synthesis involved thioglycosylation of 6-iodinated sugars with α-glycosyl thiols under phase transfer conditions. The α-configuration of glycosidic linkages was thus introduced prior to the coupling steps, and relied on the intrinsic configurational stability of α-glycosyl thiols. This work also demonstrated the great utility of MMTr as an effective anomeric S-protecting group.
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