TFA-ap-dU

Base Information

• Chemical Name: TFA-ap-dU
• CAS No.: 115899-40-6
• Molecular Formula: C14H14F3N3O6
• Molecular Weight: 377.277
• Mol file: 115899-40-6.mol

Synonyms:

Chemical Property of TFA-ap-dU

Chemical Property:

• Melting Point: >116°C (dec.)
• PKA: 8.17±0.10(Predicted)
• Density: 1?+-.0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

2''-Deoxy-5-[3-[(2,2,2-trifluoroacetyl)amino]-1-propyn-1-yl]uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2''-Deoxy-5-[3-[(2,2,2-trifluoroacetyl)amino]-1-propyn-1-yl]uridine is an intermediate in the synthesis of fluorescent labeling compounds of cyclooctyne-modified deoxyuridine triphosphates in DNA.

Technology Process of TFA-ap-dU

There total 5 articles about TFA-ap-dU 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: 88.0%

trifluoroacetyl-propargyl amine (14719-21-2) + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 2,2,2-trifluoro-N-(3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-yn-1-yl)acetamide (115899-40-6)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2008.10.093

Reference yield: 81.0%

trifluoroacetyl-propargyl amine (14719-21-2) + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 2,2,2-Trifluoro-N-{3-[1-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-prop-2-ynyl}-acetamide (115899-40-6)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jo00275a030

Reference yield: 67.0%

N-propynyltrifluoroacetamide + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + tetrakis(triphenylphosphine)palladium (0) → 2,2,2-trifluoro-N-(3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-yn-1-yl)acetamide (115899-40-6)

Guidance literature:

With triethylamine;

upstream raw materials:

trifluoroacetyl-propargyl amine

5-Iodo-2'-deoxyuridine

Downstream raw materials:

5-(3-trifluoroacetamidopropargyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine

5-(3-amino-1-propynyl)-2'-deoxyuridine 5'-triphosphate

3'-O-acetyl-5-(3''-trifluoroacetamidopropynyl)-5'-O-dimethoxytrityl-2'-deoxyuridine

5’-O-(tert-butydimethylsilyl)-5-[3-(2,2,2-trifluoroacetamido)-prop-1-ynyl]-2’-deoxyuridine

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