Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate

Base Information

• Chemical Name: Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate
• CAS No.: 3082-96-0
• Molecular Formula: C₁₅H₂₀O₁₁
• Molecular Weight: 376.317
• DSSTox Substance ID: DTXSID90453228
• Nikkaji Number: J3.180.380B
• Mol file: 3082-96-0.mol

Synonyms:3082-96-0;Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate;(3R,4S,5S,6S)-6-(METHOXYCARBONYL)TETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAYL TETRAACETATE;1,2,3,4-Tetra-O-acetyl-DGlucuronide Methyl Ester;1,2,3,4-Tetra-O-acetyl-D-glucuronide methyl ester;methyl (2S,3S,4S,5R)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate;1,2,3,4-TETRA-O-ACETYL-D-GLUCOPYRANURONIC ACID METHYL ESTER;SCHEMBL2723141;DTXSID90453228;DPOQCELSZBSZGX-BVIXPPBVSA-N;AMY41507;MFCD07357241;AS-43294;methyl tetra-o-acetyl--d-glucopyranuronate;CS-0100738;D-Glucopyranuronic acid, methyl ester, tetraacetate;1,2,3,4-Tetra-O-acetyl-?,?-D-glucuronic Acid, Methyl Ester;D-Glucopyranuronic acid, methyl ester, 1,2,3,4-tetraacetate;1-O,2-O,3-O,4-O-Tetraacetyl-D-glucopyranuronic acid methyl ester;(3R,4S,5S,6S)-6-(METHOXYCARBONYL)TETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAYLTETRAACETATE

Chemical Property of Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate

Chemical Property:

• Melting Point: 103-105°C
• Boiling Point: 412.3±45.0 °C(Predicted)
• PSA: 140.73000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: -0.75750
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 376.10056145
• Heavy Atom Count: 26
• Complexity: 584

Purity/Quality:

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

1,2,3,4-Tetra-O-acetyl-D-glucuronide methyl ester ^*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(=O)C)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](OC([C@@H]1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C
• Uses: 1,2,3,4-Tetra-O-acetyl-α,β-D-glucuronic Acid, Methyl Ester _x000D_(mixture of anomers) (cas# 3082-96-0) is a compound useful in organic synthesis.

Technology Process of Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate

There total 14 articles about Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate 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: 92.0%

methyl D-glucopyranuronate (82228-14-6) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 5h;

DOI:10.1002/ejoc.200500555

Reference yield: 77.0%

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

D-glucurono-6,3-lactone; With sodium hydroxide; In methanol; at 20 ℃; for 24h; Inert atmosphere;

acetic anhydride; With pyridine; at 10 - 20 ℃; for 4h; Inert atmosphere;

Reference yield: 77.0%

methanol (67-56-1) + D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

methanol; D-glucurono-6,3-lactone; With sodium hydroxide; at 20 ℃; for 24h; Inert atmosphere;

acetic anhydride; With pyridine; at 10 - 20 ℃; for 4h;

upstream raw materials:

methyl D-glucopyranuronate

acetic anhydride

D-(+)-glucuronic acid γ-lactone

D-glucurono-6,3-lactone

Downstream raw materials:

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester

2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester

methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate

Refernces

• 1、 Wang, Bi,Van Herck, Simon,Chen, Yong,Bai, Xiangyang,Zhong, Zifu,Deswarte, Kim,Lambrecht, Bart N.,Sanders, Niek N.,Lienenklaus, Stefan,Scheeren, Hans W.,David, Sunil A.,Kiessling, Fabian,Lammers, Twan,De Geest, Bruno G.,Shi, Yang. "Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles". supporting information. p. 12133 - 12139. Retrieved 2020/08/06.
• 2、 -. "Indole-glucoside substrate and preparation method and application thereof in detection of aerobe vaginitis (AV)". Paragraph 0016. . Retrieved 2018/09/11.