128503-39-9

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 125367-09-1 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 
• 953795-87-4 3,4,6-tri-O-benzoyl-β-D-mannopyranose-1,2-(prop-2-ynyl orthobenzoate) 
• 166241-68-5 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1521271-28-2 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 627466-98-2 2,3,4,6-tetra-O-benzoyl-α,β-D-mannospyranose 
• 934492-05-4 2,3,4,6-tetra-O-benzoyl-α,b-D-mannopyranosyl trichloroacetimidate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 14262-87-4 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 143995-68-0 2,3,4,6-tetra-O-benzoyl-β-D-selenogalactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Triflic Imide-Catalyzed Glycosylation of Disarmed Glycosyl ortho-Isopropenylphenylacetates and ortho-Isopropenylbenzyl Thioglycosides

Glycosylation reaction involving the coupling of a glycosyl donor with a glycosyl acceptor is one of the cornerstones of chemical preparation of pure glycans and glycoconjugates of biological relevance. Catalytic glycosylation of glycosyl ester donors and thioglycosides is an attractive but underexplored topic in carbohydrate chemistry. Herein, triflic imide (Tf2NH)-catalyzed glycosylation of various O-, S-, and C-nucleophiles has been achieved using disarmed glycosyl ortho-isopropenylphenylacetates (GIPPAs) and ortho-isopropenylbenzyl thioglycosides as glycosylating agents. The reactions proceed under mild conditions to give the desired glycosides in good-to-excellent yields. Of particular note, the comparable reactivity for the α-isomers and the β-ones of GIPPAs is observed. The mechanistic investigation demonstrates that the isopropenyl group is essential for the reaction and its preferential protonation triggers the reaction. This work provides another member to the arsenals of glycosyl ester and thioglycoside donors suitable for acid-catalyzed glycosylation to create various glycosidic bonds.

Investigations to mechanism and applications of the glycosylation protocol employing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycoside donors

Based on the capability of silyl ethers for efficient glycosylation, the new MTEAN glycosylation protocol utilizing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycosides as donors were extended to one-pot synthesis of nucleosides, late-stage modification of bioactive molecules, and stereoselective construction of 1,2-cis-glucosidic linkages using silyl ethers of the acceptors. Moreover, the reaction mechanism was systematically investigated by control reactions and side product characterizations, leading to the determination of a TfOH-catalyzed ynamide functionality-initiated process, which was further corroborated by identifications of the departure form of leaving group and the real catalyst.

Revisiting Glycosylations Using Glycosyl Fluoride by BF3·Et2O: Activation of Disarmed Glycosyl Fluorides with High Catalytic Turnover

Catalytic glycosylations with glycosyl fluorides using BF3·Et2O are presented. Glycosylations with both armed and disarmed donors were efficiently catalyzed by 1 mol% of BF3·Et2O in a nitrogen-filled glovebox without the use of dehydrating agents. Our finding is in sharp contrast with conventional BF3·Et2O-mediated glycosylations, where excess Lewis acid and additives are required. Mechanistic studies indicated that the chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.

Hydrogen bond activated glycosylation under mild conditions

Herein, we report a new glycosylation system for the highly efficient and stereoselective formation of glycosidic bonds using glycosyl N-phenyl trifluoroacetimidate (PTFAI) donors and a charged thiourea hydrogen-bond-donor catalyst. The glycosylation prot

8-(Methyltosylaminoethynyl)-1-naphthyl (MTAEN) Glycosides: Potent Donors in Glycosides Synthesis

With 8-(methyltosylaminoethynyl)-1-naphthyl (MTAEN) glycoside as donors, a novel and efficient glycosylation protocol has been established. The MTAEN glycosylation protocol exhibits the merits of shelf-stable donors, mild catalytic promotion conditions, considerably extended substrate scope encompassing both free alcohols, silylated alcohols, nucleobases, primary amides, and C-type nucleophile acceptors, and applicability to various one-pot strategies for highly efficient synthesis of oligosaccharides, such as orthogonal one-pot, single-catalyst one-pot, and acceptor reactivity-controlled one-pot strategies.

A Mild Glycosylation Protocol with Glycosyl 1-Methylimidazole-2-carboxylates as Donors

A mild glycosylation protocol is developed by using glycosyl 1-methylimidazole-2-carboxylates. Such a glycosylation can be promoted by a series of metal triflates and triflimides, especially Cu(OTf)2. The reaction is initiated by activation of

Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides

Presented herein is the discovery that bismuth(iii) trifluoromethanesulfonate (Bi(OTf)3) is an effective catalyst for the activation of glycosyl bromides and glycosyl chlorides. The key objective for the development of this methodology is to em

Palladium(ii)-assisted activation of thioglycosides

Described herein is the first example of glycosidation of thioglycosides in the presence of palladium(ii) bromide. While the activation with PdBr2alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylat

Ferrocenium complex aided: O-glycosylation of glycosyl halides

A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)2]SbF6 and FcBF4 as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load). This journal is

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.