(E)-5-(2-CARBOMETHOXYVINYL)-2'-DEOXYURIDINE

Base Information

• Chemical Name: (E)-5-(2-CARBOMETHOXYVINYL)-2'-DEOXYURIDINE
• CAS No.: 86163-17-9
• Molecular Formula: C13H16 N2 O7
• Molecular Weight: 312.279
• Mol file: 86163-17-9.mol

Synonyms:2-Propenoicacid, 3-[1-(2-deoxy-b-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl]-,methyl ester, (E)-; 5-((E)-2-Methoxycarbonylethenyl)-2'-deoxyuridine

Chemical Property of (E)-5-(2-CARBOMETHOXYVINYL)-2'-DEOXYURIDINE

Chemical Property:

• PKA: 8.51±0.10(Predicted)
• PSA: 130.85000
• Density: 1.540±0.06 g/cm3(Predicted)
• LogP: -1.63650
• Solubility.: Acetone; Dichloromethane; DMSO

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-5-(2-Carbomethoxyvinyl)-2’-deoxyuridine is a derivative of 5-(2-Hydroxyethyl)-2’-deoxyuridine (H942060), which is a novel type of potent antiviral nucleoside analog.

Technology Process of (E)-5-(2-CARBOMETHOXYVINYL)-2'-DEOXYURIDINE

There total 6 articles about (E)-5-(2-CARBOMETHOXYVINYL)-2'-DEOXYURIDINE 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: 100.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate (86163-17-9)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In 1,4-dioxane; for 14h; Heating;

DOI:10.1080/15257779408010680

Reference yield: 87.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 5-Iodo-2'-deoxycytidine (611-53-0) → methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate (86163-17-9)

Guidance literature:

5-Iodo-2'-deoxycytidine; With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; In water; acetonitrile; at 80 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

acrylic acid methyl ester; With triethylamine; In water; acetonitrile; at 80 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6ra19039a

Reference yield: 60.0%

5-chloromercuri-2'-deoxyuridine (65505-76-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-3-[4-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-acrylic acid methyl ester (86163-17-9)

Guidance literature:

With lithium tetrachloropalladate(II); copper dichloride; In methanol; for 3h; Ambient temperature;

DOI:10.1021/jm00363a009

upstream raw materials:

2'-deoxyuridine

acrylic acid methyl ester

5-Iodo-2'-deoxyuridine

5-Iodo-4-trimethylsilanyloxy-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine 3'-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite

5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine

(E)-5-(2-bromovinyl)-2’-deoxyuridine-5’-(1-phenylmethoxy-L-phenylalanyl)phosphate