Methyl 4'-Tosylmycophenolate

Base Information

• Chemical Name: Methyl 4'-Tosylmycophenolate
• CAS No.: 171808-02-9
• Molecular Formula: C25H28O8S
• Molecular Weight: 488.559
• DSSTox Substance ID: DTXSID90441286
• Wikidata: Q82258002
• ChEMBL ID: CHEMBL392908
• Mol file: 171808-02-9.mol

Synonyms:Methyl 4'-Tosylmycophenolate;171808-02-9;methyl (E)-6-[6-methoxy-7-methyl-4-(4-methylphenyl)sulfonyloxy-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate;Methyl 4/'-Tosylmycophenolate;CHEMBL392908;DTXSID90441286;UEHFBCOBVAUDFJ-LZYBPNLTSA-N;Methyl 4 inverted exclamation mark -Tosylmycophenolate;methyl (E) 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

Chemical Property of Methyl 4'-Tosylmycophenolate

Chemical Property:

• PSA: 113.58000
• LogP: 5.27290
• Solubility.: Dichloromethane
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 488.15048902
• Heavy Atom Count: 34
• Complexity: 853

Purity/Quality:

98% ^*data from raw suppliers

Methyl4’-Tosylmycophenolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2=C3C(=C(C(=C2CC=C(C)CCC(=O)OC)OC)C)COC3=O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2=C3C(=C(C(=C2C/C=C(\C)/CCC(=O)OC)OC)C)COC3=O
• Uses: Methyl 4’-Tosylmycophenolate (cas# 171808-02-9) is a compound useful in organic synthesis.

Technology Process of Methyl 4'-Tosylmycophenolate

There total 2 articles about Methyl 4'-Tosylmycophenolate 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: 96.0%

methyl mycophenolate (31858-66-9) + p-toluenesulfonyl chloride (98-59-9) → methyl (E) 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (171808-02-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2007.06.059

Reference yield:

mycophenolic acid (24280-93-1) → methyl (E) 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (171808-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / p-toluenesulfonic acid / 9 h / 20 °C

2: 96 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

With toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2007.06.059

Reference yield: 23.0%

methyl (E) 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (171808-02-9) → methyl (E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (171808-04-1)

Guidance literature:

With pyridine; 2,3,5-trimethyl-pyridine; lithium iodide; at 150 ℃; for 15h;

DOI:10.1016/j.bmcl.2007.06.059

upstream raw materials:

methyl mycophenolate

p-toluenesulfonyl chloride

mycophenolic acid

Downstream raw materials:

(E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid

methyl (E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoate

methyl (E) 6-(1,3-dihydro-6-ethyl-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate

Refernces

• 1、 Nelson, Peter H.,Carr, Stephen F.,Devens, Bruce H.,Eugui, Elsie M.,Franco, Fidencio,Gonzalez, Carlos,Hawley, Ronald C.,Loughhead, David G.,Milan, David J.,Papp, Eva,Patterson, John W.,Rouhafza, Sussan,Sjogren, Eric B.,Smith, David B.,Stephenson, Rebecca A.,Talamas, Francisco X.,Waltos, Ann-Marie,Weikert, Robert J.,Wu, John C.. "Structure-activity relationships for inhibition of inosine monophosphate dehydrogenase by nuclear variants of mycophenolic acid". . p. 4181 - 4196. Retrieved 2007/10/03.
• 2、 -. "6-substituted mycophenolic acid and derivatives". . . Retrieved 2008/06/13.