Synthesis of novel homo-N-nucleoside analogs composed of a homo-1,4-dioxane sugar analog and substituted 1,3,5-triazine base equivalents.
نویسندگان
چکیده
Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH(2), OH and Cl in the 2,4-triazine positions.
منابع مشابه
Enantioselective synthesis of homo-N-nucleosides containing a 1,4-dioxane sugar analog.
A dioxane homo-sugar analog, (2S,5S)-and (2R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-iodomethyl-1,4-dioxane was prepared from (2R,3R)-dimethyl tartrate, and further elaborated into the corresponding homo-N-nucleoside analogs by its reactions with uracil and adenine, respectively.
متن کاملSynthesis of a Novel Benzoyl Adenosine Analog Containing a 1, 4-Dioxane Sugar Analog and the Synthesis of a Corresponding Uracil Adenine Dinucleotide
Adenosine analogs in which the sugar unit was replaced by a 1,4-dioxane sugar equivalent, were prepared by coupling the 1,4-dioxane sugar analog as its anomeric acetates, with N6-benzoyl protected adenine. The 1,4-dioxane system was obtained in an enantioselective synthesis from (R,R)-dimethyl tartrate. Using standard phosphorimidite methodology, the adenine analog was further reacted with a 1,...
متن کاملPyrazolo[1,5-a]-1,3,5-triazine C-nucleoside as deoxyadenosine analogue: synthesis, pairing, and resistance to hydrolysis.
The synthesis of a pyrazolo[1,5-a]-1,3,5-triazine C-nucleoside (dA(PT)), designed to form two hydrogen bonds with a complementary dT residue, is reported. Oligonucleotides including this dA nucleoside analogue possess base-pairing properties similar to those of the parent oligonucleotide. This dA nucleoside analogue is more resistant to acid-catalyzed hydrolysis than dA.
متن کاملSynthesis of Pyranopyrazole Compounds Using Heterogeneous Base Catalyst Based on 1,3,5-Triazine-2,4,6-Triamine Modified Nano Rice Husk Silica
In the current study, amorphous silica nanoparticles were easily extracted from rice husk ash. The target composite was synthesized by the direct incorporation of chloropropyl groups through the condensation of nanosilica and 3-chloropropyl trimethoxysilane and then grafting of 1,3,5-triazine-2,4,6-triamine (Melamine) onto the propyl groups by the simple nucleophilic substitution reaction (RHA@...
متن کاملCombinatorial synthesis of galactosyl-1,3,5-triazines as novel nucleoside analogues.
Herein we report a parallel solid-phase synthesis of 1,3,5-triazine based nucleoside analogues by a three-step substitution, starting from 2,4,6-trichloro-1,3,5-triazine. A library of 80 galactosyl-1,3,5-triazine compounds was prepared in high purity without extensive reaction conditions or tedious purification, suggesting the generality of this method.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Molecules
دوره 13 12 شماره
صفحات -
تاریخ انتشار 2008