6-O-Methyl Mycophenolic Acid Methyl Ester

Base Information

• Chemical Name: 6-O-Methyl Mycophenolic Acid Methyl Ester
• CAS No.: 60435-90-7
• Molecular Formula: C19H24O6
• Molecular Weight: 348.396
• ChEMBL ID: CHEMBL236915
• DSSTox Substance ID: DTXSID70465263
• Nikkaji Number: J1.015.577K,J273.755H
• Mol file: 60435-90-7.mol

Synonyms:60435-90-7;6-O-Methyl Mycophenolic Acid Methyl Ester;methyl (E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate;CHEMBL236915;DTXSID70465263;methyl (4E)-6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate;6-Chloro-5-(methoxymethoxy)nicotinic Acid;(E)-Methyl 6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate;(E)-Methyl6-(4,6-dimethoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate

Chemical Property of 6-O-Methyl Mycophenolic Acid Methyl Ester

Chemical Property:

• PSA: 71.06000
• LogP: 3.12460
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 348.15728848
• Heavy Atom Count: 25
• Complexity: 514

Purity/Quality:

98% ^*data from raw suppliers

6-O-MethylMycophenolicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OC)OC
• Isomeric SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)OC)OC
• Uses: Labelled Mycophenolic Acid impurity. 6-O-Methyl Mycophenolic Acid Methyl Ester is an impurity of Mycophenolic Acid(M831500) an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleotides.Environmental contaminants; Food contaminants

Technology Process of 6-O-Methyl Mycophenolic Acid Methyl Ester

There total 14 articles about 6-O-Methyl Mycophenolic Acid 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: 90.0%

mycophenolic acid (24280-93-1) + trimethylsilyldiazomethane → 5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide (60435-90-7)

Guidance literature:

In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2007.06.059

Reference yield: 69.0%

mycophenolic acid (24280-93-1) + carbonic acid dimethyl ester (616-38-6) → 5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide (60435-90-7)

Guidance literature:

With caesium carbonate; at 160 ℃; for 72h;

DOI:10.1055/s-1998-1893

Reference yield:

6-((E)-3,7-Dimethyl-octa-2,6-dienyl)-5,7-dimethoxy-4-methyl-3H-isobenzofuran-1-one (207398-37-6) → 5,7-dimethoxy-6-(5-methoxycarbonyl-3-methyl-2-pentenyl)-4-methylphthalide (60435-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol / 3 h / -10 - 20 °C

2.1: Jones reagent / acetone / 4 h / -30 °C

3.1: 189 mg / ethyl acetate

With jones reagent; ozone; In methanol; ethyl acetate; acetone;

DOI:10.1016/S0040-4020(03)00102-9

upstream raw materials:

diazomethane

7-O-Methylmycophenolic acid

mycophenolic acid

carbonic acid dimethyl ester

Downstream raw materials:

methyl mycophenolate

7-O-Methylmycophenolic acid

mycophenolic acid

(E)-6-(3,4-Bis-hydroxymethyl-2,6-dimethoxy-5-methyl-phenyl)-4-methyl-hex-4-en-1-ol

Refernces

• 1、 Chen, Liqiang,Wilson, Daniel,Jayaram, Hiremagalur N.,Pankiewicz, Krzysztof W.. "Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylases for cancer treatment". . p. 6685 - 6691. Retrieved 2008/09/18.
• 2、 Covarrubias-Zuniga, Adrian,Gonzalez-Lucas, Armando. "A total synthesis of mycophenolic acid". . p. 2881 - 2882. Retrieved 2007/10/03.