Methyl Beta-D-Galactopyranuronate

Base Information

• Chemical Name: Methyl Beta-D-Galactopyranuronate
• CAS No.: 18490-93-2
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.168
• UNII: LQ70K1D5BW
• Wikidata: Q27465360
• ChEMBL ID: CHEMBL490226
• Mol file: 18490-93-2.mol

Synonyms:Methyl Beta-D-Galactopyranuronate;LQ70K1D5BW;UNII-LQ70K1D5BW;beta-D-Galactopyranuronic acid, methyl ester;18490-93-2;CHEMBL490226;6-O-methyl-beta-D-galacturonate;6-O-methyl-beta-D-galacturonic acid;METHYL .BETA.-D-GALACTOPYRANURONATE;.BETA.-D-GALACTOPYRANURONIC ACID, METHYL ESTER;Q27465360

Chemical Property of Methyl Beta-D-Galactopyranuronate

Chemical Property:

• XLogP3: -2
• 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: COC(=O)C1C(C(C(C(O1)O)O)O)O
• Isomeric SMILES: COC(=O)[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O)O)O)O

Technology Process of Methyl Beta-D-Galactopyranuronate

There total 7 articles about Methyl Beta-D-Galactopyranuronate 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:

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 D-galactopyranuronate (18486-47-0,18490-93-2,28817-88-1,82228-14-6) + (2S,3R,4S,5R)-3,4,5-Trihydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With boron trifluoride diethyl etherate; for 1h; Heating;

DOI:10.1039/c39950001391

Reference yield:

methanol (67-56-1) + D-galacturonic acid (685-73-4,25249-06-3,25990-10-7,36562-70-6,36655-86-4) → methyl D-galactopyranuronate (18486-47-0,18490-93-2,28817-88-1,82228-14-6)

Guidance literature:

With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In water; at 25 ℃; for 1h;

DOI:10.1016/0008-6215(93)84175-6

Reference yield:

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → methyl D-galactopyranuronate (18486-47-0,18490-93-2,28817-88-1,82228-14-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / KIO₄, RuO₂, acetone / H₂O / 2.5 h / Ambient temperature

2: 81.8 percent / DMC, pyridine / 20 h

3: AcOH, water / 12 h / Heating

With pyridine; ruthenium(IV) oxide; potassium metaperiodate; 3,3-dimethyl-D-cysteine; water; acetic acid; acetone; In water;

DOI:10.1248/cpb.41.90

upstream raw materials:

methanol

D-galacturonic acid

(3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate

D-galacturonic acid

Downstream raw materials:

(2S,3R,4S,5R)-3,4,5-Triacetoxy-6-bromo-tetrahydro-pyran-2-carboxylic acid methyl ester

D-galacturonic acid