70751-54-1

Upstream product

• 62774-33-8 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 157896-05-4 Phenyl 2,3,4,6-tetra-O-benzoyl-1-seleno-β-D-glucopyranoside 
• 183367-62-6 1-phenyltelluro-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 635727-37-6 2-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosylmercapto)-1,3-benzoxazole 
• 953795-81-8 C₃₇H₃₀O₁₀ 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 14262-85-2 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide 
• 22415-91-4 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose 
• 1038411-44-7 perbenzoyl-β-D-glucopyranosyl o-(1-hexynyl)benzoate 
• 1038411-36-7 perbenzoyl-α-D-glucopyranosyl o-(1-hexynyl)benzoate 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 1521271-26-0 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 172847-85-7 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 

Relevant academic research and scientific papers

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.

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.

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

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.

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

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

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.

Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors

A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wid

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

Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism

A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.