112289-38-0

Upstream product

• 112289-40-4 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 100-39-0 benzyl bromide 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 21193-75-9 D-galactal 
• 20672-66-6 3,4,5-tri-O-benzyl-D-galactopyranose 
• 81969-44-0 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-galactopyranose 
• 112346-75-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl chloride 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 4098-06-0 triacetyl-D-galactal 
• 112346-25-5 1,2-O-ethylidene-3,4,6-tris-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 132884-65-2 (3aS,5R,6S,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole 
• 162060-53-9 1,5-anhydro-3,4,6-tri-O-benzyl-D-galactitol 
• 851321-42-1 2-{6-(2-azido-ethoxy)-8-[4,5-bis-benzyloxy-6-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-isoindole-1,3-dione 
• 73445-27-9 methyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

A simple and highly diastereoselective preparation of glycal epoxides using the MCPBA-KF complex

Glycals are converted ro the corresponding epoxides in high yields by a diastereoselective one-step epoxidation using the m-chloroperoxybenzoic acid-KF complex in anhydrous dichloromethane.

Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

A multi-gram epoxidation of 3,4,6-tri-O-benzyl-d-glucal and d-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone/acetone in a biphasic system (CH2Cl2-aqueous NaHCO3) resulted in the formation of

C-glycosides: A stereoselective synthesis of α- and β-C-galactosides with glycosyl dianions

α- or β-C-galactosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by transmetallation of a tin compound or by reductive lithiation of a chloride. Different electrophiles react selectively at the anomeric center.

A Stereoselective and Preparative Entry to 1,2-Anhydrosugars through Oxidation of Glycals with Perfluoro-cis-2,3-dialkyloxaziridines

Perfluoro-cis-2,3-dialkyloxaziridines 1 perform the direct epoxidation of glycals 2 to give cleanly corresponding 1,2-anhydrosugars 3 with medium to complete diastereoselection; elaboration of these glycals to glycosyl fluorides and lipid conjugates is al

A short route to nucleoside diphosphate activated D- and L-hexoses

Leloir transferases utilise nucleoside diphosphate sugars, which are notoriously difficult to synthesise and handle. Starting off from D- or L-configurated glycals, a facile synthesis of nucleotide sugars by epoxidation and direct coupling with uridine di

Synthesis and Conformational Analysis of 2-O-Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides

Synthesis of orthogonally protected 2-silyl nucleosides were achieved by trans opening of sugar epoxides with nucleobases catalyzed by trimethylsilyltrifluoromethanesulfonate using hexamethyldisilazane both as solvent and silylating agent. Both α and β nu

α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether

The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.

IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS

Compounds are provided that assemble together in vivo to form an ASGPR-binding compound that has an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein.

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O

Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides

Stereoselective manipulations at the C1 anomeric position of saccharides are one of the central goals of preparative carbohydrate chemistry. Historically, the majority of reactions forming a bond with anomeric carbon has focused on reactions of nucleophiles with saccharide donors equipped with a leaving group. Here, we describe a novel approach to stereoselective synthesis of C-aryl glycosides capitalizing on the highly stereospecific reaction of anomeric nucleophiles. First, methods for the preparation of anomeric stannanes have been developed and optimized to afford both anomers of common saccharides in high anomeric selectivities. We established that oligosaccharide stannanes could be prepared from monosaccharide stannanes via O-glycosylation with Schmidt-type donors, glycal epoxides, or under dehydrative conditions with C1 alcohols. Second, we identified a general set of catalytic conditions with Pd2(dba)3 (2.5 mol%) and a bulky ligand (JackiePhos, 10 mol%) controlling the β-elimination pathway. We demonstrated that the glycosyl cross-coupling resulted in consistently high anomeric selectivities for both anomers with mono- and oligosaccharides, deoxysugars, saccharides with free hydroxyl groups, pyranose, and furanose substrates. The versatility of the glycosyl cross-coupling reaction was probed in the total synthesis of salmochelins (siderophores) and commercial anti-diabetic drugs (gliflozins). Combined experimental and computational studies revealed that the β-elimination pathway is suppressed for biphenyl-type ligands due to the shielding of Pd(II) by sterically demanding JackiePhos, whereas smaller ligands, which allow for the formation of a Pd-F complex, predominantly result in a glycal product. Similar steric effects account for the diminished rates of cross-couplings of 1,2-cis C1-stannanes with aryl halides. DFT calculations also revealed that the transmetalation occurs via a cyclic transition state with retention of configuration at the anomeric position. Taken together, facile access to both anomers of various glycoside nucleophiles, a broad reaction scope, and uniformly high transfer of anomeric configuration make the glycosyl cross-coupling reaction a practical tool for the synthesis of bioactive natural products, drug candidates, allowing for late-stage glycodiversification studies with small molecules and biologics.