1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester

Base Information

• Chemical Name: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester
• CAS No.: 5432-32-6
• Molecular Formula: C15H20 O11
• Molecular Weight: 376.317
• Mol file: 5432-32-6.mol

Synonyms:Glucopyranuronicacid, methyl ester, tetraacetate, a-D- (6CI,8CI); Methyl(1,2,3,4-tetra-O-acetyl-a-D-glucopyranosid)uronate; NSC 16926

Chemical Property of 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester

Chemical Property:

• Melting Point: 108-120 °C
• Boiling Point: 412.3°Cat760mmHg
• Flash Point: 178.4°C
• PSA: 140.73000
• Density: 1.33g/cm³
• LogP: -0.75750
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(2R,3R,4S,5S,6S)-6-(Methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayltetraacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester

There total 27 articles about 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester 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: 84.0%

methanol (67-56-1) + D-(+)-glucuronic acid γ-lactone (487-44-5) + acetic anhydride (108-24-7) → (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) + methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate (5432-32-6)

Guidance literature:

methanol; D-(+)-glucuronic acid γ-lactone; With sodium; for 4h;

acetic anhydride; With pyridine; at 4 ℃;

DOI:10.1002/anie.201806792

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;

upstream raw materials:

pyridine

glucuronic acid methyl ester

acetic anhydride

sodium acetate

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、 Chen, Yi,Li, Yanhong,Yu, Hai,Sugiarto, Go,Thon, Vireak,Hwang, Joel,Ding, Li,Hie, Liana,Chen, Xi. "Tailored design and synthesis of heparan sulfate oligosaccharide analogues using sequential one-pot multienzyme systems". . . Retrieved 2013.
• 2、 García-Oliva, Cecilia,Cabanillas, Alfredo H.,Perona, Almudena,Hoyos, Pilar,Rumbero, ángel,Hernáiz, María J.. "Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists". supporting information. p. 1588 - 1596. Retrieved 2020/02/05.
• 3、 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.