Highly Diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2.
Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and beta-(1-->6)-S-linked-thiodisaccharide synthesis. [reaction: see text].
Weng
Shiue-Shien
SS
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.
Lin
Yow-Dzer
YD
Chen
Chien-Tien
CT
D000107:Acetylation; D002384:Catalysis; D017606:Chlorine Compounds / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis; D006031:Glycosylation; D007785:Lactose / Q000737:chemistry; D008320:Maltose / Q000737:chemistry; D017895:Manganese Compounds / Q000737:chemistry*; D008752:Methylene Chloride / Q000737:chemistry; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*
D017606:Chlorine Compounds; D004187:Disaccharides; D017895:Manganese Compounds; C522757:MoO2Cl2; D010087:Oxides; D013438:Sulfhydryl Compounds; D008752:Methylene Chloride; D008320:Maltose; D007785:Lactose