114748-68-4

Basic information

• Product Name: 7-TFA-ap-7-Deaza-ddG
• Synonyms: 7-TFA-ap-7-Deaza-ddG;7-TFA-ap-7-Deaza-2',3'-dideoxyguanosine;Acetamide, N-[3-[2-amino-4,7-dihydro-4-oxo-7-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoro-7-Deaza-2', 3'-dideoxy-7-[3-[(trifluoroacetyl)amino]
• CAS NO: 114748-68-4
• Molecular Formula: C16H16F3N5O4
• Molecular Weight: 399.32
• EINECS: -0
• Mol File: 114748-68-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.67±0.1 g/cm3(Predicted)
• PKA: 9.57±0.46(Predicted)
• CAS DataBase Reference: 7-TFA-ap-7-Deaza-ddG(CAS DataBase Reference)
• NIST Chemistry Reference: 7-TFA-ap-7-Deaza-ddG(114748-68-4)
• EPA Substance Registry System: 7-TFA-ap-7-Deaza-ddG(114748-68-4)

Safety Data

• Hazardous Substances Data: 114748-68-4(Hazardous Substances Data)

Usage

General Description

7-TFA-ap-7-Deaza-ddG is a modified nucleoside that contains a seven-membered ring instead of the usual six-membered ring found in natural nucleosides. It is also fluorinated at the 7-position and has a tris(trifluoroacetate) group attached. 7-TFA-ap-7-Deaza-ddG is often used in the development and study of nucleic acid analogs and as a potential therapeutic agent. It has been found to have unique properties that make it useful for probing the structure and function of nucleic acids, as well as for developing new strategies for treating diseases such as cancer and viral infections.

Upstream product

• 14719-21-2 trifluoroacetyl-propargyl amine 
• 114748-67-3 7-iodo-2',3'-dideoxy-7-deazaguanosine 
• 114748-67-3 2-Amino-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ol 
• 114748-67-3 2-Amino-7-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 29877-76-7 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine 
• 115920-25-7 Thiocarbonic acid O-[(2R,3S,5R)-5-(4-methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester O-phenyl ester 
• 115899-60-0 5-Iodo-2-methanesulfinyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 114748-64-0 5-Iodo-4-methoxy-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 114748-65-1 5-Iodo-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 114748-62-8 (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol 
• 114748-66-2 2-Amino-5-iodo-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 114748-63-9 4-Methoxy-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 98891-39-5 7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin 

Relevant articles and documents

Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides

Coupling of iodo-nucleosides with terminal alkynes such as 3-(acylamino)propynes, whose initial products readily undergo secondary cyclization reactions, can be effected smoothly by the standard catalysis with (Ph3P)2PdCl2

Palladium-Catalyzed Synthesis of Alkynylamino Nucleosides. A Universal Linker for Nucleic Acid

A method for attaching alkynylamino "linkers" to nucleosides and nucleotides is described.Protected or unprotected alkynylamines are coupled to iodonucleosides in dimethylformamide using a 1:2 mol ratio of tetrakis(triphenylphosphine)palladium(0) and copper(I) iodide, a catalyst system superior to the standard system using palladium(II) species.The resulting alkynylamino nucleosides are useful for enzymatic or chemical labeling of all four bases of DNA.