Methyl alpha-d-glucopyranosiduronic acid

Base Information

• Chemical Name: Methyl alpha-d-glucopyranosiduronic acid
• CAS No.: 5155-45-3
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.168
• DSSTox Substance ID: DTXSID401288809
• Nikkaji Number: J686.704I
• Mol file: 5155-45-3.mol

Synonyms:methyl alpha-d-glucopyranosiduronic acid;Methyl alpha-D-glucuronide;SCHEMBL3334987;DTXSID401288809;5155-45-3

Chemical Property of Methyl alpha-d-glucopyranosiduronic acid

Chemical Property:

• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 208.05830272
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)C(=O)O)O)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O

Technology Process of Methyl alpha-d-glucopyranosiduronic acid

There total 27 articles about Methyl alpha-d-glucopyranosiduronic acid 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: 25.0%

methyl α-D-gluco-hexodialdo-1,5-pyranoside (23598-27-8) → methyl α-D-glucopyranosiduronic acid (5155-45-3)

Guidance literature:

With sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dihydrogen peroxide; In water; for 24h; pH=5;

Reference yield: 7.0%

methyl-alpha-D-glucopyranoside (97-30-3) → methyl α-D-gluco-hexodialdo-1,5-pyranoside (23598-27-8) + methyl α-D-glucopyranosiduronic acid (5155-45-3)

Guidance literature:

With sulfuric acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; In water; at 20 ℃; for 48h; pH=0.5 - 1.5;

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → formic acid (64-18-6) + glycolic Acid (79-14-1) + methyl α-D-gluco-hexodialdo-1,5-pyranoside (23598-27-8) + methyl α-D-glucopyranosiduronic acid (5155-45-3) + D-erythronic acid (488-16-4) + D-glucaric acid (87-73-0,7231-46-1)

Guidance literature:

With oxygen; platinum on activated charcoal; In water; at 49.9 ℃; under 300.02 Torr; Product distribution; Mechanism; initial rate of consumption, pH effect;

DOI:10.1016/S0008-6215(97)00157-2

upstream raw materials:

C₄₄H₆₄O₁₆

licorice-saponin D₃

licorice-saponin A₃

methyl beta-D-glucopyranoside

Downstream raw materials:

D-glucuronic acid

methyl β-D-glucuronopyranoside methyl ester

XYLITOL

1-O-methyl-α-D-glucopyranuronic acid methyl ester

Refernces

• 1、 Yin, Y. Ben,Chen, Li,Heck, Kimberly N.,Zhang, Z. Conrad,Wong, Michael S.. "Toward glucuronic acid through oxidation of methyl-glucoside using PdAu catalysts". . . Retrieved 2019/12/11.
• 2、 Costa, Carina,Alves, Anabela,Pinto, Paula R.,Sousa, Rui A.,Borges Da Silva, Eduardo A.,Reis, Rui L.,Rodrigues, Alírio E.. "Characterization of ulvan extracts to assess the effect of different steps in the extraction procedure". experimental part. p. 537 - 546. Retrieved 2012/06/15.