A practical and efficient synthesis of phosphatidylinositol pentamannoside （PIM5） was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two re...A practical and efficient synthesis of phosphatidylinositol pentamannoside （PIM5） was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two regioselective sequential glycosylations on inositol and p-tolyl thioglycosides as the sole type of building blocks made this protocol to avoid the tedious protective group manipulations. This synthetic strategy provides access to other important glycolipids with similar structures.展开更多
A family of the 3,6-branched Fuziα-glucans including the pentasaccharide repeating unit as well as its di-and trimers were efficiently achieved via a one-pot and convergent glycosylation strategy.All the protectedα-...A family of the 3,6-branched Fuziα-glucans including the pentasaccharide repeating unit as well as its di-and trimers were efficiently achieved via a one-pot and convergent glycosylation strategy.All the protectedα-glucans up to 15-mer were assembled with high yields and excellentα-stereoselectivity,which was secured by the synergisticα-directing effects of the Tol SCl/Ag OTf promotion system and the stericβ-facial shielding of bulky saccharide residues linked at the 6-O-position of glucosyl donors.Moreover,the 3,6-branched architecture of glycosyl donor was revealed to be more favorable for theα-selective glucosidation of primary hydroxyl group,especially in the case of large oligosaccharide acceptor.The structurally well-defined syntheticα-glucans would be useful for various biological studies.展开更多
An antimetastatic tetrasaccharide β-D-Gal-（1 → 4）-β-D- GlcpNAc-（1 →6）-α-D-Manp-（1 → 6）-β-D-Manp-OMe, was syn- thesized with two approaches. The first approach was a conventional method employing thioglyc...An antimetastatic tetrasaccharide β-D-Gal-（1 → 4）-β-D- GlcpNAc-（1 →6）-α-D-Manp-（1 → 6）-β-D-Manp-OMe, was syn- thesized with two approaches. The first approach was a conventional method employing thioglycoside and Koenigs-Knorr glycosylation reaction in 24% overall yield. The second one was a novel route through the azidoiodo-glycosylation strategy by using 2-iodo-2-deoxylactosyl azide as the donor in 36% overall yield.展开更多
Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins w...Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins were synthesized in mild condition with excellent yields.展开更多
基金financially supported by the National Natural Science Foundation of China(Nos.21232002,21572012,and 21772006)Beijing Natural Science Foundation(No.2142015)Beijing Higher Education Young Elite Teacher Project(No.YETP0063)
文摘A practical and efficient synthesis of phosphatidylinositol pentamannoside （PIM5） was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two regioselective sequential glycosylations on inositol and p-tolyl thioglycosides as the sole type of building blocks made this protocol to avoid the tedious protective group manipulations. This synthetic strategy provides access to other important glycolipids with similar structures.
基金supported by the National Natural Science Foundation of China(No.22177060)the Young Scholars Program of Shandong University(No.2018WLJH41)+1 种基金the Open Projects Fund of Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology,Shandong University(No.2021CCG06)the Central Government Guide Local Science and Technology Development Funds(No.YDZX20203700002579)。
文摘A family of the 3,6-branched Fuziα-glucans including the pentasaccharide repeating unit as well as its di-and trimers were efficiently achieved via a one-pot and convergent glycosylation strategy.All the protectedα-glucans up to 15-mer were assembled with high yields and excellentα-stereoselectivity,which was secured by the synergisticα-directing effects of the Tol SCl/Ag OTf promotion system and the stericβ-facial shielding of bulky saccharide residues linked at the 6-O-position of glucosyl donors.Moreover,the 3,6-branched architecture of glycosyl donor was revealed to be more favorable for theα-selective glucosidation of primary hydroxyl group,especially in the case of large oligosaccharide acceptor.The structurally well-defined syntheticα-glucans would be useful for various biological studies.
基金supported by the National Basic Research Program of China(973 program,No.2012CB822100)the National Natural Science Foundation of China(No.20972012)
文摘An antimetastatic tetrasaccharide β-D-Gal-（1 → 4）-β-D- GlcpNAc-（1 →6）-α-D-Manp-（1 → 6）-β-D-Manp-OMe, was syn- thesized with two approaches. The first approach was a conventional method employing thioglycoside and Koenigs-Knorr glycosylation reaction in 24% overall yield. The second one was a novel route through the azidoiodo-glycosylation strategy by using 2-iodo-2-deoxylactosyl azide as the donor in 36% overall yield.
基金Financial support of this research from the National Natural Science Foundaion of China(20372085)is gratefully acknowledged by the authors.
文摘Using thioglycosides as donors, trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N-iodosuccinimide(NIS) as promoter, a modified procedure for the glycosylation of spirostanol was developed. A series of saponins were synthesized in mild condition with excellent yields.
