169557-99-7

Basic information

• Product Name: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate
• Synonyms: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate;1,2,3-TRI-O-BENZOYL-4,6-DIDEOXY-4-IODO-ALPHA-L-GLUCOPYRANOSE;Methyl2,3,4-tri-O-benzoyl-a-D-glucopyranuronosyltrichloroacetimidate;a-D-Glucopyranuronic acid, methyl ester, 2,3,4-tribenzoate 1-(2,2,2-trichloroethanimidate);2,3,4-Tri-O-benzoyl-α-D-glucopyranuronic acid methyl ester, trichloroacetimidate;2,3,4-Tri-O-benzoyl-alpha-D-glucuronide methyl ester trichloroacetimidate;2,3,4-Tri-O-benzoyl-a-D-glucuronide methyl ester trichloroacetimidate
• CAS NO: 169557-99-7
• Molecular Formula: C₃₀H₂₄Cl₃NO₁₀
• Molecular Weight: 664.87126
• EINECS: 1533716-785-6
• Product Categories: Sugars;Carbohydrates & Derivatives;Intermediates
• Mol File: 169557-99-7.mol

Chemical Properties

• Melting Point: 136-139°C
• Boiling Point: 685.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: 1.39±0.70(Predicted)
• Stability: Acid Sensitive, Temperature Sensitive
• CAS DataBase Reference: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate(169557-99-7)
• EPA Substance Registry System: 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate(169557-99-7)

Safety Data

• Hazardous Substances Data: 169557-99-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate is used as a synthetic intermediate for the preparation of various complex organic molecules, particularly in the field of carbohydrate chemistry. The compound's unique structure and reactivity make it a valuable building block for the synthesis of biologically active molecules, natural products, and potential pharmaceutical candidates.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate is used as a key intermediate for the development of novel drug candidates. Its structural features allow for the creation of diverse chemical entities with potential therapeutic applications, such as anti-inflammatory, anti-cancer, or anti-infective agents.
Used in Glycobiology Research:
2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate is also utilized in glycobiology research to study the role of carbohydrates in biological processes and their interactions with proteins, lipids, and other biomolecules. The compound can be used to probe the structure and function of glycoconjugates, which are essential components of cell surfaces and extracellular matrices.
Used in Material Science:
In the field of material science, 2,3,4-Tri-O-benzoyl-alpha-D-glucopyranuronic acid methyl ester trichloroacetimidate can be employed to develop novel carbohydrate-based materials with specific properties, such as enhanced biocompatibility, biodegradability, or self-assembly capabilities. These materials can find applications in various areas, including drug delivery, tissue engineering, and sensors.

Upstream product

• 545-06-2 trichloroacetonitrile 
• 548477-88-9 methyl (2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate) 
• 98-88-4 benzoyl chloride 
• 87924-24-1 benzyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 291528-10-4 benzyl 6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 
• 220608-60-6 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzoyloxy-6-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 220608-55-9 C₅₀H₄₈O₉Si 
• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 2595-07-5 allyl β-D-glucopyranoside 
• 1228755-40-5 C₄₆H₄₆O₉Si 
• 866325-70-4 allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 103674-69-7 methyl 2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-α-D-glucopyranuronate 
• 82228-14-6 methyl D-glucopyranuronate 

Downstream Products

• 635684-69-4 4-methoxyphenyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranuronate)-(1→3)-4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 677767-21-4 4-methoxyphenyl O-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-O-benzoyl-4,6-O-di-tert-butylsilylene-β-D-galactopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 213327-16-3 C₇₈H₈₇NO₂₀ 
• 34096-83-8 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid 

Relevant articles and documents

Chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG)

The invention discloses a chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG), and belongs to the fields of organic synthesis, medicinal chemistry, and food science. Abundant and cheap glycyrrhetinic acid is taken as the primary raw material, and GAMG is simply and easily synthesized by following five steps: carboxyl to benzyl ester conversion, glycosidation between C3 hydroxyl groups and a fully benzoylated methyl glucuronate glycosyl donor, methyl removal, benzoyl removal, and benzyl removal. The raw materials and reagents are cheap, the reaction conditions aremild, the operation is simple, the yield is good, and the GAMG chemical synthesis method is feasible.

Synthesis of glucuronic acid derivatives via the efficient and selective removal of a C6 methyl group

This investigation is related to the development of a general strategy for the synthesis of certain glucuronic acid derivatives. In particular, we report exceptionally selective conditions for removing the C6 methyl protecting group by potassium hydroxide

Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4

Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful. Copyright