4291-69-4

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE
• Synonyms: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE;2,3,4,6-TETRA-O-BENZYL-A-D-GALACTOPYRANOSE, 99% MIN. HPLC;2,3,4,6-TETRA-O-BENZYL-A-D-GALACTOPYRANOSE;2,3,4,5-Tetra- O-benzyl-a-D-galactopyranose;a-D-Galactopyranose, 2,3,4,6-tetrakis-O-(phenylMethyl)-
• CAS NO: 4291-69-4
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.65
• Mol File: 4291-69-4.mol
• Article Data: 162

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 672.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• PKA: 11.87±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(4291-69-4)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE(4291-69-4)

Safety Data

• Hazardous Substances Data: 4291-69-4(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranose is a chemical compound that is commonly used as a building block in organic synthesis. It is a derivative of galactose, a type of sugar. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GALACTOPYRANOSE is often employed in the production of various pharmaceuticals and other organic molecules due to its ability to be modified and transformed into different structures. The benzyl groups attached to the galactose molecule provide protection and stability, allowing for selective reactions to take place. Overall, 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranose is a crucial component in the development of a wide range of organic compounds.

Upstream product

• 13096-63-4 2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid 
• 115969-49-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 128785-05-7 Dimethyl-phenyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-silane 
• 67540-18-5 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 201409-35-0 prop-1-(Z)-enyl 2',3',4',6'-tetra-O-benzyl-β-D-glucopyranoside 
• 83238-56-6 3,4,6-tri-O-benzyl-1,2-O-<(S)-benzylidene>-α-D-glucopyranose 
• 83238-55-5 3,4,6-tri-O-benzyl-1,2-O-<(R)-benzylidene>-α-D-glucopyranose 
• 4291-68-3 1-chloro-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 744246-05-7 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 99388-26-8 benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 67-56-1 methanol 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 

Downstream Products

• 53929-48-9 (2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 116417-79-9 phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 116417-80-2 phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 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 
• 74808-15-4 (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 78890-65-0 (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 146773-71-9 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 92052-34-1 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-dichloracetimidat 
• 92052-34-1 O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-dichloracetimidat 
• 92414-03-4 Iodo-acetic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 

Relevant articles and documents

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.

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.

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.