1418031-58-9Relevant academic research and scientific papers
Structure-based design of a highly constrained nucleic acid analogue: Improved duplex stabilization by restricting sugar pucker and torsion angle γ
Hanessian, Stephen,Schroeder, Benjamin R.,Giacometti, Robert D.,Merner, Bradley L.,Ostergaard, Michael,Swayze, Eric E.,Seth, Punit P.
, p. 11242 - 11245 (2012)
Dual conformational restriction: A new, highly constrained modification of the α-L-locked nucleic acid (α-L-LNA) scaffold that locks the sugar furanose ring in an N-type configuration and also restricts rotation around torsion angle γ was synthesized (see scheme). This new modification increases the thermostability of an oligonucleotide duplex compared to using a single mode of constraint alone. Copyright
Synthesis of a carbohydrate-derived 1-oxaspiro[4.4]nonane skeleton and its conversion into spironucleosides
Maity, Joy Krishna,Achari, Basudeb,Drew, Michael G. B.,Mandal, Sukhendu B.
experimental part, p. 2533 - 2542 (2010/09/08)
An easy entry to the 1-oxaspiro[4.4]nonane skeleton has been developed starting from a d-glucose-derived substrate. The key steps involve (a) installation of olefin moieties at the appropriate places through simple transformations and (b) construction of spiro rings by utilizing ring-closing metathesis reactions between these olefin functionalities. Subsequent deprotection of the acetonide functionality, peracetylation, nucleosidaton under Vorbrggen reaction conditions, and final deprotections result in the formation of the spironucleosides. The involvement of an interesting intra/intermolecular acetyl migration has been used to rationalize the product distribution during desilylation. Various 1D and 2D NMR techniques and X-ray analyses of some important intermediates were used for assigning the structures and stereochemistry of the products. Georg Thieme Verlag Stuttgart New York.
Introduction of vinyl and hydroxymethyl functionalities at C-4 of glucose-derived substrates: Synthesis of spirocyclic, bicyclic, and tricyclic nucleosides
Maity, Joy Krishna,Ghosh, Ramprasad,Drew, Michael G. B.,Achari, Basudeb,Mandal, Sukhendu B.
, p. 4305 - 4308 (2008/09/20)
(Chemical Equation Presented) Installing hydroxymethyl and hydroxyethyl substitutions at C-4 through vinylation and hydroboration-oxidation reactions of the C-4 bis-hydroxymethyl derivative of D-glucose based substrate, and inserting heteroatoms thereafter permitted formation of N-, O-, or S-heterocycles leading to [4,5]-or [5,5]-spirocycles and a bicyclo[3.3.0]octane product. Some of the spirocycles were converted to spironucleosides under Vorbrueggen glycosidation reaction conditions. Similarly, the bicyclic product was elaborated to the corresponding bicyclic nucleoside as well as an unexpected tricyclic nucleoside.
