119898-64-5Relevant academic research and scientific papers
Improved protocol for the synthesis of flexibly protected morpholino monomers from unprotected ribonucleosides
Pattanayak, Sankha,Paul, Sibasish,Nandi, Bappaditya,Sinha, Surajit
, p. 763 - 782 (2013/01/16)
An inexpensive and much improved protocol has been developed for the synthesis of protected morpholino monomers from unprotected ribonucleosides in high overall yield, using oxidative glycol cleavage and reductive amination strategy. Unlike the previous methods, the present strategy allows installing the exocyclic amine protections at a later stage, and thus avoids the use of expensive, or commercially unavailable, exocyclic amine-protected ribonucleosides as starting materials. To demonstrate the flexibility of the present method in choosing protecting groups, the monomers have been protected with several such groups of different deblocking properties at the exocyclic amine position.
Total synthesis of a cyclic adenosine 5′-diphosphate ribose receptor agonist
Swarbrick, Joanna M.,Potter, Barry V. L.
experimental part, p. 4191 - 4197 (2012/06/18)
Stable cyclic adenosine 5′-diphosphate ribose (cADPR) analogues are chemical biology tools that can probe the Ca2+ release mechanism and structure-activity relationships of this emerging potent second messenger. However, analogues with an intac
MORPHOLINO-BASED ANTISENSE AGENT
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Page/Page column 16, (2012/12/13)
Morpholino-based oligomers suitable as antisense agent comprising modifications of phosphorodiamidate backbone or modification with 5-substituted pyrimidines of morpholino compound that is soluble in culture medium and sufficient for cell penetration thereby eliminating the need for injecting into the cells. Monomers comprising the said oligomers and its method of manufacture, method of manufacture of the said oligomers and its dye, flurophore, drug, biomolecule conjugate wherein the said oligomers find different end use but not limited to regulation of gene expression, tissue culture with improved transfection efficiency and related studies on cellular transfection.
Nucleic acid related compounds. 105. Synthesis of 2',3'-didehydro- 2',3'-dideoxynucleosides from ribonucleoside cyclic 2',3'-(Sulfates or phosphates) or 2',3'-dimesylates via reductive elimination with sodium naphthalenide
Robins, Morris J.,Lewandowska, Elzbieta,Wnuk, Stanislaw F.
, p. 7375 - 7381 (2007/10/03)
Treatment of purine ribonucleosides with thionyl fluoride resulted in formation of cyclic 2',3'-sulfite esters. Acetylation of the 5'-hydroxy group and Sharpless oxidation (NaIO4/RuCl3) gave the cyclic 2',3'-sulfate ester derivatives. Treatment of 5'-O-silyl-protected ribonucleosides with thionyl chloride followed by oxidation gave an alternative route to the cyclic 2',3'- sulfates. Reductive elimination with sodium naphthalenide (THF/-50 °C) gave the 2',3'-unsaturated nucleosides. Parallel treatment of adenosine cyclic 2',3'-phosphate gave the 2',3'-olefin. The adenine, hypoxanthine, and 2- amino-6-methoxypurine 2',3'-didehydro-2',3'-dideoxynucleosides were prepared efficiently (40-60% overall yields of crystalline, analytically pure products; 3-5 steps, some combined into one-flask procedures) by treatment of 5'-O-protected 2',3'-di-O-mesylribonucleosides with sodium naphthalenide. Reactions were performed at or below ambient temperature with readily available reagents and standard laboratory conditions.
THE CHEMISTRY OF 2',3'-SECONUCLEOSIDES III. SYNTHESIS AND REACTIONS OF PURINE-2',3'-SECORIBONUCLEOSIDES
Beaton, Graham,Jones, Stanley A.,Walker, Richard T.
, p. 6419 - 6428 (2007/10/02)
5'-O-Protected purine-ribonucleosides were oxidised with periodate to give dialdehydes which upon reduction with sodium borohydride gave 5'-O-protected purine-2',3'-secoribonucleosides, which were converted into their 2',3'-di-O-mesyl derivatives.These we
