Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D-

Base Information

• Chemical Name: Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D-
• CAS No.: 3082-95-9
• Molecular Formula: C₁₃H₁₈O₁₀
• Molecular Weight: 334.28
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID80953020
• Mol file: 3082-95-9.mol

Synonyms:Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D-;(2S,3S,4S,5R)-3,4,5-triacetyloxy-6-methoxyoxane-2-carboxylic acid;SCHEMBL7622321;DTXSID80953020;E83278;Methyl 2,3,4-tri-O-acetylhexopyranosiduronic acid

Chemical Property of Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D-

Chemical Property:

• Vapor Pressure: 1.27E-08mmHg at 25°C
• Melting Point: 103-105oC
• Boiling Point: 430.6°Cat760mmHg
• PKA: 11.23±0.70(Predicted)
• Flash Point: 154.3°C
• PSA: 134.66000
• Density: 1.37g/cm³
• LogP: -1.32830
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 334.08999677
• Heavy Atom Count: 23
• Complexity: 487

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3,4-Tri-O-acetyl-D-glucuronicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC)C(=O)O)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1OC(=O)C)OC)C(=O)O)OC(=O)C
• Uses: May contain a minor amount of the beta isomer 2,3,4-Tri-O-acetyl-D-glucuronic Acid Methyl Ester (cas# 3082-95-9) is a compound useful in organic synthesis.

Technology Process of Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D-

There total 3 articles about Glucopyranuronic acid, methyl ester, 2,3,4-triacetate, D- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

p-Coumaric Acid (7400-08-0,50940-26-6) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → methyl 1-O-[2'(E)-3'-(4''-hydroxyphenyl)-2'-propenoyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2005.06.029

Reference yield: 23.0%

→ 2-monochlorophenol (95-57-8) + 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester (3082-95-9,72692-06-9,73464-50-3)

Guidance literature:

Reference yield:

4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester (861966-16-7) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → 4-[5-((2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yloxy)-pyridin-2-yl]-piperazine-1-carboxylic acid benzyl ester (915207-11-3) + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -60 - 23 ℃; for 41h; Title compound not separated from byproducts;

DOI:10.1021/jo0611972

upstream raw materials:

p-Coumaric Acid

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester

Downstream raw materials:

1-O-2-(4-Chlorphenoxy)-2-methyl-propionyl-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[2-(benzyl-methyl-amino)-propyl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2R,4aR,6S,7R,8R,8aS)-7-azido-6-benzoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester