5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine

Base Information

• Chemical Name: 5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine
• CAS No.: 58931-19-4
• Molecular Formula: C13H16N2O8
• Molecular Weight: 328.27
• DSSTox Substance ID: DTXSID40705623
• Mol file: 58931-19-4.mol

Synonyms:58931-19-4;SCHEMBL6888282;DTXSID40705623;5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine

Chemical Property of 5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine

Chemical Property:

• PSA: 151.08000
• LogP: -2.66570
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 328.09066547
• Heavy Atom Count: 23
• Complexity: 572

Purity/Quality:

99%min ^*data from raw suppliers

(E)-5-(2-Carbomethoxyvinyl)uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: COC(=O)C=CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Uses: (E)-5-(2-Carbomethoxyvinyl)uridine can be used as a reactant/reagent in preparation of modified nucleosides, nucleotides, and nucleic acids, and uses thereof for human granulocyte-colony stimulating factor-modified mRNA-induced cell proliferation.

Technology Process of 5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine

There total 5 articles about 5-(3-Methoxy-3-oxoprop-1-en-1-yl)uridine 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: 86.0%

5-iodouridine (1024-99-3) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3-(5-uridinyl)propenoate (58931-19-4)

Guidance literature:

With palladium diacetate; TEA; triphenylphosphine; for 1h; Heating;

DOI:10.1021/jm00152a008

Reference yield: 47.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + uridine (58-96-8) → methyl 3-(5-uridinyl)propenoate (58931-19-4)

Guidance literature:

With palladium diacetate; In acetonitrile; for 72h; Heating;

DOI:10.1055/s-1987-27981

Reference yield: 38.0%

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one (111582-84-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3-(5-uridinyl)propenoate (58931-19-4)

Guidance literature:

In acetonitrile; for 24h; Irradiation;

upstream raw materials:

5-iodouridine

acrylic acid methyl ester

1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-5-iodo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

uridine

Downstream raw materials:

(E)-5-(2-bromovinyl)uridine

(E)-5-(2-carboxyvinyl)uridine

Refernces

• 1、 -. "Sulfur-containing uridine anticancer compound and intermediate and preparation method thereof". Paragraph 0040; 0061; 0062; 0063; 0064. . Retrieved 2016/10/09.
• 2、 Hirota, Kosaku,Isobe, Yoshiaki,Kitade, Yukio,Maki, Yoshifumi. "A Simple Synthesis of 5-(1-Alkenyl)uracil Derivatives by Palladium-Catalyzed Oxidative Coupling of Uracils With Olefins". . p. 495 - 496. Retrieved 2007/10/02.