132748-02-8

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE
• Synonyms: 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE;2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate;2,3,4,6-Tetrakis-O-(phenylMethyl)-D-galactopyranose 2,2,2-TrichloroethaniMidate
• CAS NO: 132748-02-8
• Molecular Formula: C₃₆H₃₆Cl₃NO₆
• Molecular Weight: 685.03
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 132748-02-8.mol

Chemical Properties

• Melting Point: 78-79°C
• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetone, Chloroform, DMSO, Methanol
• Stability: Store in Freezer
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE(132748-02-8)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE(132748-02-8)

Safety Data

• Hazardous Substances Data: 132748-02-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE is used as a synthetic intermediate for the preparation of complex organic molecules, particularly in the field of carbohydrate chemistry. Its unique structure allows for the selective protection and deprotection of hydroxyl groups, facilitating the synthesis of various glycoconjugates and oligosaccharides.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE is used as a key building block for the synthesis of glycoconjugate drugs and drug candidates. These glycoconjugates have potential applications in the treatment of various diseases, including cancer, infectious diseases, and autoimmune disorders, due to their ability to modulate immune responses and target specific cells.
Used in Material Science:
2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE can also be used in material science for the development of novel materials with specific properties. For example, it can be used to synthesize glycopolymers and glycoconjugated nanoparticles with potential applications in drug delivery, diagnostics, and biomaterials.
Used in Research and Development:
In the field of research and development, 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE TRICHLOROACETIMIDATE serves as a valuable tool for studying the structure, function, and interactions of carbohydrates in biological systems. It can be used to probe the role of carbohydrates in cell recognition, signaling, and adhesion, as well as to investigate the mechanisms of carbohydrate processing and metabolism.

Upstream product

• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 545-06-2 trichloroacetonitrile 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 143536-99-6 p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 12167-34-9 p-methoxyphenyl d-mannoside 
• 83-87-4 D-Mannose pentaacetate 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3458-28-4 D-Mannose 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 

Downstream Products

• 215869-71-9 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2S,3R,5R,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyloxy)-tetrahydro-pyran 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 38768-84-2 dibenzyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl phosphate 
• 90357-98-5 dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 
• 103383-07-9 (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 103368-05-4 (3β,5β,14β,17β)-3β-<(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 194594-79-1 allyl 2,3,4,6-tetrabenzyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside 
• 136984-86-6 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-mannopyranoside 
• 136984-91-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 1373416-90-0 (2S)-3-cyclohexyl-2-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)naphthalen-7-yloxy]propionic acid 
• 1373416-88-6 (2S)-3-cyclohexyl-2-[2-hydroxy-1-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)naphthalen-7-yloxy]propionic acid 
• 1373416-77-3 (2S)-3-cyclohexyl-2-[2-hydroxy-1-(2,3,4,6-tetra-O-benzyl-α-D-mannpyranosyl)naphthalen-7-yloxy]propionic acid methyl ester 
• 1373416-82-0 (2S)-3-cyclohexyl-2-[2-hydroxy-1-(-D-mannopyranosyl)naphthalen-7-yloxy]propionic acid 

Relevant articles and documents

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

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.

Visible-Light-Mediated β-C(sp3)-H Amination of Glycosylimidates: En Route to Oxazoline-Fused/Spiro Nonclassical Bicyclic Sugars

A straightforward route has been developed for the diastereoselective synthesis of nonclassical conformationally constrained oxazoline-fused and spiro bicyclic sugars bearing a quaternary center via selective β-C-H amination of appropriately positioned gl

An Empirical Understanding of the Glycosylation Reaction

Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.

Carbohydrate-lipid constructs and their use in preventing or treating viral infection

The invention relates to selected carbohydrate-lipid constructs and their use as mimics of ligands for receptors expressed by virus. In particular, the invention relates to the use of selected carbohydrate-lipid constructs in methods of inhibiting virus infection and/or promoting clearance of virus from infected subjects. Carbohydrate-lipid constructs selected for use in these methods where the virus is Human Immunodeficiency Virus (HIV) are provided.

Efficient α-mannosylation of phenols: The role of carbamates as scavengers for activated glycosyl donors

The boron trifluoride activation of trichloroacetimidate donors was found to be an efficient method for the α-mannosylation of tyrosine-containing acceptors. Most notably, these conditions are compatible with the commonly used carbamate protecting groups, whereas trichloroacetimidate activation with trimethylsilyl triflate or the use of glycosyl sulfoxides led to diminished yields in the presence of carbamates. In these cases, the competing reaction of the activated donors with the carbamate group was identified as a problematic side reaction. Taking advantage of this reactivity, various glycosyl carbamates were generated for the first time under non-acidic glycosylation conditions by reaction of different Boc-protected amino acids and dipeptides with glycosyl sulfoxides under triflic anhydride activation. Georg Thieme Verlag Stuttgart · New York.

Fluorine-directed β-galactosylation: Chemical glycosylation development by molecular editing

Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1). Copyright

Monosaccharidic mimetics of the sialyl LewisX tetrasaccharide based on 2,7-dihydroxynaphthalene

A potential monosaccharidic mimetic of the sialyl LewisX tetrasaccharide (sLeX) was identified based on an in silico docking study using the crystal structure of an E-selectin-sLeX complex. The chemical synthesis of the mimetic in an ortho-selective C-glycosylation is described. This compound and two close analogues were evaluated in a cell-based selectin binding assay where none of the tested mimetics showed an IC 50 below 1mM. This result can be explained by an unexpected 1C4 conformation of the mannosyl residue which precludes the required binding of the Ca2+-ion in E-selectin.

β-selective C-mannosylation of electron-rich phenols

The reaction of tetra-O-benzylmannosyl trichloroacetimidate with electron-rich phenols in the presence of TMSOTf surprisingly leads to the exclusive formation of aryl β-C-glycosides while a preference for the -anomer could be observed with other Lewis aci

Glycosylation catalyzed by a chiral bronsted acid

"Chemical equation presented" The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochem