alpha-D-Galactopyranosiduronic acid, methyl, methyl ester

Base Information

• Chemical Name: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester
• CAS No.: 5155-54-4
• Molecular Formula: C₈H₁₄O₇
• Molecular Weight: 222.19
• DSSTox Substance ID: DTXSID101031449
• Nikkaji Number: J109.433E
• Mol file: 5155-54-4.mol

Synonyms:.alpha.-D-Galactopyranosiduronic acid, methyl, methyl ester;Galactopyranosiduronic acid, methyl, methyl ester, .alpha.-D-;5155-54-4;Dimethyl hexopyranosiduronate #;DCXMXXNUXSBWDI-FPJCOBNTSA-N;DTXSID101031449;Methyl(methyl .alpha.-d-mannopyranoside)uronate;Methyl alpha-D-galactopyranosiduronic acid methyl ester;1-O-Methyl-alpha-D-galactopyranuronic acid methyl ester;alpha-D-Galactopyranosiduronic acid, methyl, methyl ester;methyl (2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxane-2-carboxylate

Chemical Property of alpha-D-Galactopyranosiduronic acid, methyl, methyl ester

Chemical Property:

• Storage Temp.: Refrigerator
• Solubility.: Water
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 222.07395278
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

1-O-Methyl-β-D-glucuronideMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)C(=O)OC)O)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)C(=O)OC)O)O)O
• Uses: 1-O-Methyl-β-D-glucuronide Methyl Ester is a carbohydrate derivative used in various synthesis of pharmaceutical significant compounds.

Technology Process of alpha-D-Galactopyranosiduronic acid, methyl, methyl ester

There total 19 articles about alpha-D-Galactopyranosiduronic acid, methyl, methyl ester 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 (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate (83075-41-6) → methyl (methyl α-D-galacturonopyranoside)uronate (5155-54-4,528584-66-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; formic acid;

DOI:10.1007/BF00580445

Reference yield: 50.0%

methanol (67-56-1) + D-galacturonic acid (489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) → methyl (methyl α-D-galacturonopyranoside)uronate (5155-54-4,528584-66-9)

Guidance literature:

With hydrogenchloride; for 5h; Heating;

Reference yield: 48.0%

methanol (67-56-1) + D-galacturonic acid (6294-16-2) → methyl (methyl α-D-galacturonopyranoside)uronate (5155-54-4,528584-66-9)

Guidance literature:

With acetyl chloride; In methanol; Reflux;

DOI:10.1021/ja209067v

upstream raw materials:

methanol

D-galacturonic acid

D-galacturonic acid

methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate

Downstream raw materials:

methyl (methyl 3,4-O-isopropylidene-α-D-galactopyranoside)uronate

O¹,O²-dimethyl-α-D-galactopyranuronic acid amide

benzyl 1-O-acetyl 2,3,4-tri-O-benzyl-α-D-galactopyranuronate

benzyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)uronate

Refernces

• 1、 Jongkees, Seino A. K.,Withers, Stephen G.. "Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases". supporting information; experimental part. p. 19334 - 19337. Retrieved 2012/01/31.
• 2、 Schnatbaum, Karsten,Sch?fer, Hans J.. "Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO". . p. 864 - 872. Retrieved 2007/10/03.