7-TFA-ap-7-Deaza-ddA

Base Information

• Chemical Name: 7-TFA-ap-7-Deaza-ddA
• CAS No.: 114748-71-9
• Molecular Formula: C₁₆H₁₆F₃N₅O₃
• Molecular Weight: 383.33
• DSSTox Substance ID: DTXSID201101550
• Mol file: 114748-71-9.mol

Synonyms:114748-71-9;7-TFA-ap-7-Deaza-ddA;Acetamide, N-[3-[4-amino-7-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoro-;N-[3-[4-amino-7-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidin-5-yl]prop-2-ynyl]-2,2,2-trifluoroacetamide;N-[3-[4-Amino-7-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoro-Acetamide;DTXSID201101550;N-(3-(4-Amino-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)prop-2-yn-1-yl)-2,2,2-trifluoroacetamide;N-(3-{4-amino-7-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}prop-2-yn-1-yl)-2,2,2-trifluoroacetamide;AKOS030627029;AC-32278;HY-138588;CS-0159242;J-700297;N-[3-[4-Amino-7-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide

Chemical Property of 7-TFA-ap-7-Deaza-ddA

Chemical Property:

• Melting Point: 167-169 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 650.9±55.0 °C(Predicted)
• PKA: 9.63±0.46(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 383.12052388
• Heavy Atom Count: 27
• Complexity: 619

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(OC1CO)N2C=C(C3=C(N=CN=C32)N)C#CCNC(=O)C(F)(F)F
• Isomeric SMILES: C1C[C@@H](O[C@@H]1CO)N2C=C(C3=C(N=CN=C32)N)C#CCNC(=O)C(F)(F)F

Technology Process of 7-TFA-ap-7-Deaza-ddA

There total 6 articles about 7-TFA-ap-7-Deaza-ddA 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: 92.0%

trifluoroacetyl-propargyl amine (14719-21-2) + [(S)-5-(4-Amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydro-furan-2-yl]-methanol (114748-70-8) → N-{3-[4-Amino-7-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide (114748-71-9)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; for 4h;

DOI:10.1021/jo00275a030

Reference yield: 90.0%

trifluoroacetyl-propargyl amine (14719-21-2) + 7-deaza-2',3'-dideoxy-7-iodoadenosine (114748-70-8) → 7-deaza-2',3'-dideoxy-7-(3-trifluoroacetamidopropyn-1-yl)adenosine (114748-71-9)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; for 6h; Ambient temperature;

DOI:10.1016/S0040-4039(00)97456-2

Reference yield:

2',3'-dideoxytubercidin (40627-30-3) → 7-deaza-2',3'-dideoxy-7-(3-trifluoroacetamidopropyn-1-yl)adenosine (114748-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Hg(OAc)2 2) I₂

2: Et₃N / (Ph₃P)4Pd, CuI / dimethylformamide / 4 h / Ambient temperature

With mercury(II) diacetate; iodine; triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

upstream raw materials:

trifluoroacetyl-propargyl amine

7-deaza-2',3'-dideoxy-7-iodoadenosine

2-Acetoxy-2-methyl-propionic acid (2R,3S,4S,5R)-4-acetoxy-5-(4-amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3-bromo-tetrahydro-furan-2-ylmethyl ester

tubercidin