title: Expedient synthesis of an α-S-(1→6)-linked pentaglucosyl thiol.
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.
authors.affiliation: College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
authors.forename: Huali
authors.initials: H
authors.lastname: Wang
authors.forename: Xiangming
authors.initials: X
authors.lastname: Zhu
mesh_terms: D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013863:Thioglucosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D013438:Sulfhydryl Compounds; D013863:Thioglucosides