13322-90-2

Upstream product

• 165877-99-6 2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 2280-44-6 D-Glucose 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 

Downstream Products

• 13145-23-8 methyl 3,4,6-tri-O-benzoyl-2-deoxy-α-D-arabino-hexopyranoside 
• 13145-18-1 methyl 3,4,6-tri-O-benzoyl-2-deoxy-β-D-arabino-hexapyranose 
• 79999-45-4 (+)-(5S,6R)-5-(Benzoyloxy)-6-(benzoyloxymethyl)-5,6-dihydro-2H-pyran-2-one 
• 122359-39-1 C₂₇H₂₁ClO₈ 
• 39706-30-4 C₂₉H₂₈O₉ 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 117136-21-7 3,4,6-tri-O-benzoyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose 
• 101857-04-9 3,4,6-tri-O-benzoyl-2-deoxy-α,β-D-glucopyranose 
• 1260029-13-7 C₄₇H₆₂O₆ 
• 1260105-07-4 SAC-0518 
• 1376271-20-3 C₂₃H₂₀O₅ 
• 1376271-38-3 C₂₃H₂₀O₅ 
• 1469874-77-8 1-(4,6-di-O-benzoyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-phenylacetylene 
• 1469874-78-9 C₃₄H₂₆O₅ 

Relevant academic research and scientific papers

Oxidative addition of secondary C-X bonds to palladium(0): A beneficial anomeric acceleration

The oxidative addition of secondary electrophiles to Pd(0) is significantly accelerated by anomeric effects. In contrast to cyclohexyl bromide, acetobromo-α-d-glucose undergoes invertive oxidative addition to tris(triethylphosphine)palladium(0) to generate a stable, isolable organometallic complex, Pd(PEt3)2(Br)(AcO-β-glucose), which has been fully characterized but is prone to β-acetoxy elimination.

Electrochemical formation of glycals in THF

A new method is presented to produce unsaturated sugars from glycosyl bromides. This work offers a simplification of existing electrochemical approaches to these types of species and is amenable to scale up for large-scale production. In addition, this work is intended to provide a means of employing electrochemistry that can be duplicated in most organic chemistry laboratories using readily available glassware and equipment.

Practical synthesis of 2-deoxy sugars via metal free deiodination reactions

2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b

Rhodium-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides

Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenative transannulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to exc

The synthesis of rare earth metal-doped upconversion nanoparticles coated with d-glucose or 2-deoxy-d-glucose and their evaluation for diagnosis and therapy in cancer

Rare earth metal-doped upconversion nanoparticles (UCNPs) are emerging as a new class of biomedical imaging materials due to their higher energy anti-Stokes shift, high optical penetration depth and long term repetitive imaging. In the present study, upconversion nanoparticles based on NaYF4 doped with thulium (Tm) and ytterbium (Yb) were prepared via a thermolysis method using oleic acid as a capping agent and 1-octadecene as a solvent. The X-ray diffraction pattern of the synthesized nanoparticles was found to match the standard hexagonal phase. The nanoparticles were coated with silica using tetraethyl orthosilicate (TEOS) and in order to avoid agglomeration, IGEPAL CO-520 was used as the surfactant. The coatings of SiO2 over NaYF4 were confirmed by the TEM image and XRD pattern. NaYF4@SiO2 was further functionalized by the addition of (3-aminopropyl)trimethoxysilane (APTMS) followed by either d-glucose or 2-deoxy-d-glucose (2-DG). UCNPs-d-glucose and UNCPs-2DG were examined for cell viability (MCF-7 cells) by MTT assay. The cellular uptake of UCNPs in MCF-7 cells was seen in terms of emission of a blue light. Furthermore, the uptake rate of UCNPs coated with 2-deoxy-d-glucose was found to be much faster than that of UCNPs alone under d-glucose starved conditions. The functionalization of UCNPs with 2-deoxy-d-glucose (2-DG) not only increased the uptake of nanoparticles, but also blocked the glycolysis pathway resulting in the inhibition of tumor growth as 2-deoxy-d-glucose (2-DG) is mimicking the d-glucose. The results are indicative that these upconversion nanoparticles may find applications in bio-imaging, removal of tumor by precision surgery, therapy and targeted drug delivery. This journal is

Method for preparing 3,4,6-tri-O-substituent-D-glucal

The invention discloses a method for preparing 3,4,6-tri-O-substituent-D-glucal. The method comprises the following steps: (1) preparation of D-glucal: subjecting 3,4,6-tri-O-acetyl-D-glucal, which serves as a starting raw material, to a reaction under al

TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

Preparation method of glycal

The invention belongs to the technical field of chemical engineering and discloses a preparation method of glycal. The method comprises the following steps: (1) adding an organic solvent into a reactor equipped with polyhydroxyaldehyde monosaccharide and a catalyst in an atmosphere of nitrogen, adding a hydroxyl protective agent, carrying out a reflux reaction, and carrying out subsequent processing to obtain a compound a; (2) successively adding ammonium salt and an organic solvent into the compound a under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound b; (3) letting the compound b, substituted hydrazine and a water-removal additive into an organic solvent under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound c; and (4) adding a catalyst and the compound c dissolved in the organic solvent into alkali under the condition of nitrogen, reacting, and carrying out subsequent processing so as to obtain glycal. The preparation method is simple and easy to operate, is low-cost and environment-friendly, and has market advantages. Meanwhile, yield of glycal prepared by the preparation method is good.

An efficient method for the synthesis of pyranoid glycals

A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.

A rapid synthesis of pyranoid glycals promoted by β-cyclodextrin and ultrasound

A convenient and environmentally benign procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β-cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid- or base-sensitive and disaccharide glycosyl bromides. A yield of 85%-96% of glycals was obtained. Copyright