2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate
• CAS No.: 92420-89-8
• Molecular Formula: C15H18 Cl3 N O10
• Molecular Weight: 478.668
• Hs Code.: 2932990090
• European Community (EC) Number: 692-083-0
• Nikkaji Number: J1.233.091J
• Mol file: 92420-89-8.mol

Synonyms:92420-89-8;2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate;(2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate;MFCD02094293;2,3,4-Tri-O-acetyl-alpha-D-glucuronide methyl ester trichloroacetimidate;methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate;C15H18Cl3NO10;SCHEMBL8068962;KWNIVSQDHXVNAL-HKLXJQGRSA-N;AKOS026674289;AS-11172;2,3,4-Tri-O-acetyl--D-glucuronide methyl ester trichloroacetimidate;2,3,4-Tri-O-acetyl-?-D-glucuronic Acid Methyl Ester Trichloroacetimidate;2,3,4-Tri-O-acetyl- alpha -D-glucuronic Acid Methyl Ester, Trichloroacetimidate;Methyl 1-O-trichloroacetimidoyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate;Trichloroacetimidic acid 2-O,3-O,4-O-triacetyl-6-O-methyl-alpha-D-glucopyranuronosyl ester;(2S,3S,4S,5R,6R)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of 2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 103-105掳C
• Refractive Index: 1.555
• Boiling Point: 442.115°C at 760 mmHg
• PKA: 1.39±0.70(Predicted)
• Flash Point: 221.183°C
• PSA: 147.51000
• Density: 1.595g/cm³
• LogP: 1.14320
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 476.999629
• Heavy Atom Count: 29
• Complexity: 680

Purity/Quality:

98% ^*data from raw suppliers

2,3,4-Tri-O-acetyl-a-D-glucuronide methyl ester trichloroacetimidate ^*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(=N)C(Cl)(Cl)Cl)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@@H]([C@@H]1OC(=O)C)OC(=N)C(Cl)(Cl)Cl)C(=O)OC)OC(=O)C

Technology Process of 2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate

There total 13 articles about 2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester, Trichloroacetimidate 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: 93.0%

→ methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8)

Guidance literature:

Reference yield: 83.0%

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) + trichloroacetonitrile (545-06-2) → methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

DOI:10.1016/S0008-6215(03)00317-3

Reference yield: 82.0%

2,3,4-tri-O-acetyl-β-D-glucuronic acid methyl ester (77668-10-1) + trichloroacetonitrile (545-06-2) → methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8)

Guidance literature:

With polymer-supported 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.201002798

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

trichloroacetonitrile

1α-hydroxy-2,3,4-triacetyl-α-D-glucopyranuronate methyl ester

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[5-bromo-2-(4-fluoro-phenyl)-thiophen-3-yl]-5-methanesulfonyl-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

O²,O³,O⁴-triacetyl-O¹-(2-oxo-2H-chromen-7-yl)-β-D-glucopyranuronic acid methyl ester

methyl {(17β-acetoxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

Refernces

• 1、 Hayes, John A.,Eccles, Kevin S.,Elcoate, Curtis J.,Daly, Carla A.,Lawrence, Simon E.,Moynihan, Humphrey A.. "Crystal polymorphism of Methyl 2,3,4-tri-O-acetyl-1-O- (trichloroacetimidoyl)-α-d-glucopyranouronate". . p. 138 - 143. 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、 -. "PDE10 INHIBITORS AND RELATED COMPOSITIONS AND METHODS". Page/Page column 20; 21. . Retrieved 2016/11/14.