230631-18-2Relevant academic research and scientific papers
Biocatalytic route to C-4′-spiro-oxetano-xylofuranosyl pyrimidine nucleosides
Rungta, Pallavi,Mangla, Priyanka,Khatri, Vinod,Maity, Jyotirmoy,Prasad, Ashok K.
, p. 458 - 468 (2018/02/28)
A facile access to C-4′-spiro-oxetano-xylofuranosyl nucleosides has been demonstrated for the first time through Lipozyme TL IM-mediated regioselective acetylation of one of the primary hydroxyl group over the other primary and secondary hydrox
XYLO-LNA ANALOGUES
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Page/Page column 22, (2010/05/13)
A bicyclic nucleoside derivative, wherein an intranucleoside ring locks the ring conformation of the nucleoside, is termed an LNA - a Locked Nucleic Acid. LNAs of the xylo-configuration, considered useful as therapeutic agents, diagno
L-RIBO-LNA ANALOGUES
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Page/Page column 25, (2010/11/26)
From EXEMP_CLAIMS : An oligomer comprising at least one nucleoside analogue of the general formula I wherein X is selected from -O-, -S-, -N(RN*)-, -C(R6R6*)-; B is selected from hydrogen, hydroxy, optionally substituted C1-4-alkoxy, optionally substituted C1-4-alkyl, optionally substituted C1-4-acyloxy, nucleobases, DNA intercalators, photochemically active groups, thermochemically active groups, chelating groups, reporter groups, and ligands; P designates the radical position for an internucleoside linkage to a succeeding monomer, or a 5''-terminal group, such internucleoside linkage or 5''-terminal group optionally including the substituent R5 or equally applicable the substituent R5*; P* designates an internucleoside linkage to a preceding monomer, or a 3''-terminal group; R2* and R4* together designate a biradical consisting of 1-4 groups/atoms selected from -C(RaRb)-, -C(Ra)=C(Ra)-, -C(Ra)=N-, -O-, -Si(Ra)2-, -S-, -SO2-, -N(Ra)-, and >C=Z, wherein Z is selected from -O-, -S-, and -N(Ra)-, and Ra and Rb each is independently selected from hydrogen, optionally substituted C1-12-alkyl, optionally substituted C2-12-alkenyl, optionally substituted C2-12-alkynyl, hydroxy, C1-12-alkoxy, C2-12-alkenyloxy, carboxy, C1-12-alkoxycarbonyl, C1-12-alkylcarbonyl, formyl, aryl, aryloxy-carbonyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryloxy-carbonyl, heteroaryloxy, heteroarylcarbonyl, amino, mono- and di(C1-6-alkyl)amino, carbamoyl, mono- and di(C1-6-alkyl)-amino-carbonyl, amino-C1-6-alkylaminocarbonyl, mono- and di(C1-6-alkyl)amino-C1-6-alkyl-aminocarbonyl, C1-6-alkylcarbonylamino, carbamido, C1-6-alkanoyloxy, sulphono, C1-6-alkylsulphonyloxy nitro, azido, sulphanyl, C1-6-alkylthio, halogen, DNA intercalators, photochemically active groups, thermochemically active groups, chelating groups, reporter groups, and ligands, where aryl and heteroaryl may be optionally substituted, and where two geminal substituents Ra and Rb together may designate optionally substituted methylene olefin (=CH2); each of the substituents R1*, R2, R3*, R5, R5*, R6, and R6* which are present is independently selected from hydrogen, optionally substituted C1-12-alkyl, optionally substituted C2-12-alkenyl, optionally substituted C2-12-alkynyl, hydroxy, C1-12-alkoxy, C2-12-alkenyloxy, carboxy, C1-12-alkoxycarbonyl, C1-12-alkylcarbonyl, formyl, aryl, aryloxy-carbonyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryloxy-carbonyl, heteroaryloxy, heteroarylcarbonyl, amino, mono- and di(C1-6-alkyl)amino, carbamoyl, mono- and di(C1-6-alkyl)-amino-carbonyl, amino-C1-6-alkyl-aminocarbonyl, mono- and di(C1-6-alkyl)amino-C1-6-alkyl-aminocarbonyl, C1-6-alkyl-carbonylamino, carbamido, C1-6-alkanoyloxy, sulphono, C1-6-alkylsulphonyloxy, nitro, azido, sulphanyl, C1-6-alkylthio, halogen, DNA intercalators, photochemically active groups, thermochemically active groups, chelating groups, reporter groups, and ligands, where aryl and heteroaryl may be optionally substituted, and where two geminal substituents together may designate oxo, thioxo, imino, or optionally substituted methylene, or together may form a spiro biradical consisting of a 1-5 carbon atom(s) alkylene chain which is optionally interrupted and/or terminated by one or more heteroatoms/groups selected from -O-, -S-, and -(NRN)- where RN is selected from hydrogen and C1-4-alkyl, and where two adjacent (non-geminal) substituents may designate an additional bond resulting in a double bond; and RN*, when present is selected from hydrogen and C1-4-alkyl; and basic salts and acid addition salts thereof.
Synthesis and restricted furanose conformations of three novel bicyclic thy mine nucleosides: A xylo-LNA. nucleoside, a 3'-0,5'-Cmethylene-linked nucleoside, and a 2′-0,5′-C-methylene-linked nucleoside
Rajwanshi, Vivck K.,Ktimar, Ravindra,Kofod-Hansen, Mikael,Wengel, Jesper
, p. 1407 - 1414 (2007/10/03)
The xylo-LNA nucleoside 1-(2-O,4-C-methylene-β-D-xyIofuranosyl)thymine (9) and the 2′-0,5′-C-methylene linked nucleoside 1-(2,6-anhydro-β-D-altrofuranosyI)thymine (28) were obtained in overall yields of 13% (8 steps) and 31% (7 steps) starting from furanose derivatives 1 and 21, respectively. In the synthesis of 3′-O,5′-C-methylene-linked nucleoside derivatives, cyclization by intramolecular attack from the 6-hydroxy group on the 3-keto functionality to give C-3-hemiketal furanose 11 and its subsequent transformation into nucleoside 15 proved very efficient. It was, however, impossible to isolate the debenzylated 2'-hydroxy, 2'-O-methyl and 2'-O-ter/-butyldimethylsiIyl derivatives 16,18 and 20, respectively, in analytically pure form. Solution-phase conformational analysis showed the bicyclic nucleosides 8,9,14,15,17 and 19 to exist predominantly in an N-type furanose conformation and bicyclic nucleotides 27 and 28 to adopt an S-type conformation.
