6386-24-9

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2,3,4,6-Tetra-O-benzyl-D-galactopyranose is used as a protecting group in the synthesis of complex carbohydrate molecules for pharmaceutical research and drug development. Its ability to selectively protect hydroxyl groups allows for the controlled modification of other functional groups within the molecule, facilitating the synthesis of desired carbohydrate structures with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3,4,6-tetra-O-benzyl-D-galactopyranose is used as a versatile building block for the preparation of various complex organic compounds. Its benzyl-protected hydroxyl groups enable selective reactions and transformations, making it a valuable intermediate in the synthesis of a wide range of organic molecules.
Used in the Synthesis of Glycosides:
2,3,4,6-Tetra-O-benzyl-D-galactopyranose is also used in the synthesis of glycosides, which are important molecules in various biological processes. Glycosides are formed by the condensation of a sugar molecule with another organic compound, and the selective protection of hydroxyl groups in 2,3,4,6-tetra-O-benzyl-D-galactopyranose allows for the controlled formation of specific glycosidic linkages. These glycosides have applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, 2,3,4,6-tetra-O-benzyl-D-galactopyranose serves as a model compound for studying the reactivity and selectivity of sugar derivatives. Its benzyl-protected hydroxyl groups provide a platform for investigating various chemical reactions and transformations, contributing to the understanding of carbohydrate chemistry and the development of new synthetic strategies.

Upstream product

• 136215-68-4 2,3,4,6,1',3',4'-hepta-O-benzyl-6'-O-tert-(butyldiphenylsilyl)sucrose 
• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 150-76-5 4-methoxy-phenol 
• 87908-20-1 2-methoxyethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 67890-29-3 benzyl 2,3,4,6-tetra-O-benzyl-β-D-gluco-pyranoside 
• 117307-17-2 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside sulfoxide 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 16001-93-7 tetramethyl methylenediphosphonate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 849834-71-5 2-(phenylsulfonyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 67-56-1 methanol 
• 50256-33-2 n-pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 87908-21-2 2-methoxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl>-β-D-fructopyranose 
• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl>-β-D-fructopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 74808-06-3 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-N,2,2-triphenylacetimidat 
• 74808-05-2 2,3,4,6-tetra-O-benzyl-1-O-(N-4-methylphenyl)diphenylacetimidyl-β-D-glucopyranose 
• 92414-02-3 2,3,4,6-tetra-O-benzyl-1-O-bromoacetyl-β-D-glucopyranose 
• 129318-98-5 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-bis(2-hydroxy-4,5-methylenedioxyphenyl)-D-glucitol 
• 85422-87-3 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one 
• 82598-89-8 ethyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate 
• 82598-90-1 ethyl 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)acetate 
• 82614-10-6 ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 
• 116183-75-6 ethyl 2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 

Relevant academic research and scientific papers

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Method for continuously synthesizing benzyl-substituted glucolactone by adopting microchannel reaction device

The invention discloses a method for continuously synthesizing benzyl-substituted glucolactone by adopting a microchannel reaction device. The method comprises the following steps: taking methyl-alpha-D-mannopyranoside as an initial raw material, preparing the methyl-alpha-D-mannopyranoside into an old organic solvent solution, and reacting the old organic solvent solution with an organic solvent solution of benzyl chloride in a first microreactor to generate methyl glucose with hydroxyl protected by benzyl; reacting a homogeneous solution formed by mixing a reaction solution of benzyl-substituted gluconic acid and a small amount of hydrochloric acid solution in a second microreactor for demethylation to generate hydroxyl benzyl-substituted glucose; and finally, reacting the reaction solution with an aqueous solution of hydrogen peroxide and sodium hydroxide and an organic solvent solution of tetramethylpiperidine nitrogen oxide in a third microreactor to generate the high-purity hypoglycemic drug Dapagliflozin intermediate benzyl substituted glucolactone. The method disclosed by the invention is higher in heat and mass transfer efficiency and easier to industrially amplify, the initial materials are simple, cheap and easily available, the process is simple, the obtained intermediate is high in purity and high in yield, the production cost can be effectively reduced, and the method is suitable for industrial production.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.

Synthesis and conformational analysis of vicinally branched trisaccharide β-d-Galf-(1 → 2)-[β-d-Galf-(1 → 3)-]-α-GalpfromCryptococcus neoformansgalactoxylomannan

The synthesis of a vicinally branched trisaccharide composed of twod-galactofuranoside residues attachedviaβ-(1 → 2)- and β-(1 → 3)-linkages to the α-d-galactopyranoside unit has been performed for the first time. The reported trisaccharide represents the galactoxylomannan moiety first described in 2017, which is the capsular polysaccharide of the opportunistic fungal pathogenCryptococcus neoformansresponsible for life-threatening infections in immunocompromised patients. The NMR-data reported here for the synthetic model trisaccharide are in good agreement with the previously assessed structure of galactoxylomannan and are useful for structural analysis of related polysaccharides. The target trisaccharide as well as the constituent disaccharides were analyzed by a combination of computational and NMR methods to demonstrate good convergence of the theoretical and experimental results. The results suggest that the furanoside ring conformation may strongly depend on the aglycon structure. The reported conformational tendencies are important for further analysis of carbohydrate-protein interaction, which is critical for the host response towardC. neoformansinfection.

Regioselective Anomeric O-Benzyl Deprotection in Carbohydrates

A highly regioselective hydrogenolysis of the anomeric benzyl group is reported. The reaction involves selective acetolysis of benzyl acetals of various mono- and di-saccharides using 10 % Pd/C under hydrogen atmosphere in the presence of Na2CO

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors

We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.