121238-27-5

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate
• Synonyms: α-D-Mannopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethaniMidate);[(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(2,2,2-trichloroethanimidoyl)oxy-tetrahydropyran-2-yl]methyl acetate
• CAS NO: 121238-27-5
• Molecular Formula: C₁₆H₂₀Cl₃NO₁₀
• Molecular Weight: 492.69
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 121238-27-5.mol
• Article Data: 100

Chemical Properties

• Melting Point: 62-64℃
• Boiling Point: 463.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 1.39±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate(121238-27-5)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate(121238-27-5)

Safety Data

• Hazardous Substances Data: 121238-27-5(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyltrichloroacetimidate is a complex organic compound with the chemical formula C18H21Cl3NO9. It is a syrupy substance that is primarily used in organic synthesis due to its unique chemical properties.

Uses

Used in Organic Synthesis:
2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyltrichloroacetimidate is used as a synthetic intermediate for the preparation of various complex carbohydrates and glycoconjugates. Its application in organic synthesis is due to its ability to facilitate the formation of glycosidic bonds, which are crucial for the structure and function of many biological molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyltrichloroacetimidate is used as a key building block for the synthesis of glycoconjugate drugs. These drugs 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 cell receptors.
Used in Research and Development:
2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyltrichloroacetimidate is also utilized in research and development for the study of carbohydrate chemistry, glycobiology, and the development of new glycosylation methods. Its use in research helps to advance the understanding of the role of carbohydrates in biological processes and the development of novel therapeutic strategies.
Used in Material Science:
In material science, 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyltrichloroacetimidate can be used as a component in the development of advanced materials with specific properties, such as self-assembly, recognition, and targeting capabilities. These materials have potential applications in drug delivery, sensors, and other high-tech industries.

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 545-06-2 trichloroacetonitrile 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 13242-53-0 acetobromomannose 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 57884-82-9 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 7296-15-3 alpha-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 

Downstream Products

• 128377-05-9 benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 128377-03-7 benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 151413-76-2 Octyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,4-di-O-benzyl-β-D-mannopyranosid 
• 139494-05-6 Octyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2-O-benzyl-4-desoxy-β-D-lyxopyranosid 
• 139494-02-3 Octyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2-O-benzyl-4-O-methyl-β-D-mannopyranoside 
• 139523-74-3 Octyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-2-O-benzyl-4-O-methyl-β-D-mannopyranosid 
• 143669-63-0 O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-O-(2-benzyl-4-O-methyl-β-D-mannopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-desoxy-β-D-glucopyranose 
• 121256-22-2 methyl 4-O-acetyl-3-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-mannopyranoside 
• 123826-50-6 p-methoxyphenyl 3,6-di-O-benzyl-2-O-p-methylbenzoyl-α-D-mannopyranoside 
• 126403-26-7 p-methoxyphenyl 3,6-di-O-benzyl-2,4-di-O-p-methylbenzoyl-α-D-mannopyranoside 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of bifunctional cationic compound for gene delivery

Bifunctional cationic compound carrying trivalent galactosides as the cell targeting ligand and DAB-dendr-(NH2)8 (generation 2.0) as the DNA binding domain was synthesized for gene delivery to hepatocytes. DAB-dendr-(NH2)4 (generation 1.0) conjugated with a hydrocarbon chain was used as a scaffold for the attachment of three galactosides, while the other hydrocarbon end was linked with DAB-dendr-(NH2)8 (generation 2.0) through a carbamate bond. This design provided an effective entry for the synthesis of a polyamine compound having the cell targeting galactosyl ligand. Preliminary in vitro transfection results demonstrated that the bifunctional cationic compound could effectively deliver the gene into HepG2 cells.

Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks

Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.

Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides

Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-derived oligosaccharides: one is 3-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,3-glycosidic bound, the other is 1-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,1-glycosidic bound, which were accomplished in seven steps from d-fructose and β-d-galactose and every step of yield above 75%. This synthetic route provided a practical and effective synthetic strategy for galactooligosaccharides, starting from commercially available monosaccharides. Then we evaluated on their prebiotic properties in the search for potential agents of regulating and improving the intestinal flora of human. The result showed that the prebiotic properties of Lactulose-derived oligosaccharides was much better than Lactulose. Among them, 3-O-β-d-galactopyranosyl-d-fructose displayed the most potent activity of proliferation of L. acidophilus.

A study of polymer-supported bases for the solution phase synthesis of glycosyl trichloroacetimidates

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Glycopolymer-Grafted Nanoparticles: Synthesis Using RAFT Polymerization and Binding Study with Lectin

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1,2,3,4-TETRAHYDROQUINOXALINE DERIVATIVE, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF

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An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

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