118545-30-5

Upstream product

• 104707-00-8 methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 953795-81-8 C₃₇H₃₀O₁₀ 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

A new, powerful glycosylate method: Activation of thioglycosides with dimethyl disulfide-triflic anhydride

(Formula Presented) Dimethyl disulfide reacts with triflic anhydride to provide a highly reactive electrophile. Various thioglycosides, differing in their thio aglycons, carbohydrate units, and protecting group pattern, were activated with Me2S

NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides

Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed.

Ortho-(1-phenylvinyl)benzoate glycosylation donor, and preparation method and application thereof

The invention discloses an ortho-(1-phenylvinyl)benzoate glycosylation donor, and a preparation method and an application thereof in a glycosylation reaction. The ortho-(1-phenylvinyl)benzoate glycosylation donor is stable, is easy to prepare and store, and is widely applied to the construction of various oxygen glucosides and nucleoside (nitrogen glucoside) glycosidic bonds. The leaving group ofthe donor is an alkenyl ester, has a high activity, and can be combined with thioglycoside or n-pentenyl ether glucoside through a one-pot glycosylation reaction to synthesize oligosaccharide. The glycosylation reaction conditions are mild, and receptors sensitive to acid and electrophilic reagents can tolerate the glycosylation reaction conditions.

N-Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

For the first time, N-trifluoromethylthiosaccharin was used to activate thioglycosides in the presence of catalytic amounts of TMSOTf. The results show that the activated thioglycosides undergo glycosidation reactions with various glycosyl acceptors to gi

Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides

Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a

Hybrid solution/solid-phase synthesis of oligosaccharides by using trichloroacetyl isocyanate as sequestration-enabling reagent of sugar alcohols

(Chemical Equation Presented) An excess of glycosyl acceptor is used in the solution-phase synthesis of oligosaccharides and any unconverted acceptor is removed by using trichloroacetyl isocyanate. A levulinoyl (Lev) ester group is then used as a masked tag in the following "resin-capture-release" purification strategy (see scheme).