(2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide

Base Information

• Chemical Name: (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide
• CAS No.: 370595-48-5
• Molecular Formula: C₅₇H₆₅N₅O₁₁
• Molecular Weight: 996.17
• Mol file: 370595-48-5.mol

Synonyms:(2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide

Chemical Property of (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide

There total 12 articles about (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide 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: 53.0%

(+)-5'-O-(4,4'-dimethoxytrityl)-6-[2-(methoxycarbonyl)ethenyl]-2'-deoxyuridine (370595-47-4) + N-(6-aminohexyl)-2-[3-(4-nitrophenyl)-1-adamantyl]acetamide hydrochloride → (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide (370595-48-5)

Guidance literature:

(+)-5'-O-(4,4'-dimethoxytrityl)-6-[2-(methoxycarbonyl)ethenyl]-2'-deoxyuridine; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 2h;

N-(6-aminohexyl)-2-[3-(4-nitrophenyl)-1-adamantyl]acetamide hydrochloride; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4020(03)00875-5

Reference yield:

N-(6-amino-hexyl)-2-[3-(4-nitro-phenyl)-adamantan-1-yl]-acetamide (370595-54-3) + (E)-3-(3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acrylic acid → (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide (370595-48-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/S0040-4039(01)01091-7

Reference yield:

tert-butyl N-(6-aminohexyl)carbamate (51857-17-1) → (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide (370595-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / N-hydroxybenxotriazole; triethylamine; EDAC / CH₂Cl₂ / 5 h / 20 °C

2.1: HCl / dioxane / 45 h / 20 °C

3.1: LiOH*H₂O; H₂O / tetrahydrofuran / 2 h / 20 °C

3.2: 53 percent / triethylamine; N-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / dimethylformamide / 20 °C

With hydrogenchloride; lithium hydroxide; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/S0040-4020(03)00875-5

upstream raw materials:

N-(6-amino-hexyl)-2-[3-(4-nitro-phenyl)-adamantan-1-yl]-acetamide

(+)-5'-O-(4,4'-dimethoxytrityl)-6-[2-(methoxycarbonyl)ethenyl]-2'-deoxyuridine

tert-butyl N-(6-aminohexyl)carbamate

2-[3-(4-nitrophenyl)-1-adamantyl]acetic acid