116113-69-0

Upstream product

• 67-63-0 isopropyl alcohol 
• 343565-46-8 (BnO)4Gal-β-N-tosylcarbamate 
• 343565-47-9 (BnO)4Gal-β-N,N-(methyl)tosylcarbamate 
• 343565-48-0 (BnO)4Gal-β-N,N-(cyanomethyl)tosylcarbamate 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 92470-93-4 (2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 103368-06-5 2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 1-O-trichloroacetimidate 
• 109-99-9 tetrahydrofuran 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 

Relevant academic research and scientific papers

A new glycosylation strategy for the synthesis of mannopyranosides

Activation of the anomeric centre of 1-O-2,3,4,6-tetra-O-benzyl-D-mannopyranosyl propane-1,3-diyl phosphate in the presence of trimethylsilyl triflate allowed the preparation of α- or β-manno-linked glycosides. Copyright (C) 2000 Elsevier Science Ltd.

A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel

Visible light promoted method for constructing O-glycoside bonds

The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, t

Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy

The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.

Modular and stereoselective synthesis of C-aryl glycosides via Catellani reaction

In this work, we describe a Catellani-type C-H glycosylation to provide rapid access to various highly decorated α-C-(hetero)aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside-pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.

N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors

A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O–glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the β-selectivity.

An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group

An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a