51549-37-2Relevant academic research and scientific papers
A facile method for detritylation of 5'-O-dimethoxy-trityl-3'-O-tert-butyldimethylsilyl-2'-deoxynucleosides
Patil,Mane,Salunkhe
, p. 2423 - 2428 (1994)
The dimethoxytrityl group can be removed effectively from 5'-O-dimethoxytrityl-3'-O-tert-butyl dimethylsilyl-2'-deoxynucleosides and their N-acyl derivatives by using sulfonated crosslinked (1% DVB) polystyrene in dichloromethane-methanol (97.5:2.5, v/v)
Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides
Baran, Phil S.,Eastgate, Martin D.,Knouse, Kyle W.,Padial, Natalia M.,Rivas-Bascón, Nazaret,Schmidt, Michael A.,Vantourout, Julien C.,Xu, Dongmin,Zheng, Bin
supporting information, (2020/03/30)
Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorus-Sulfur Incorporation reagents previously disclosed. Here, the adaptable phosphorus(V) scaffold enables sequential addition of carbon nucleophiles to produce a variety of enantiopure C-P building blocks. Addition of three carbon nucleophiles to Π, followed by stereospecific reduction, affords useful P-chiral phosphines; introduction instead of a single methyl group reveals the first stereospecific synthesis of methylphosphonate oligonucleotide precursors. While both Π enantiomers are available, only one isomer is required - the order of nucleophile addition controls the absolute stereochemistry of the final product through a unique enantiodivergent design.
A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid
Huang, Hua-Shan,Kong, Rui,Zheng, Xiu-An,Chen, Wei-Jie,Han, Shuai-Bo,Zeng, De-Yun,Gong, Shan-Shan,Sun, Qi
supporting information, p. 2437 - 2443 (2018/11/23)
In nucleoside/nucleotide chemistry, the regioselective cleavage of 5′-O-TBS groups of persilylated nucleosides is a desired approach for structural functionalization at the 5′-position. However, efficient and practical methods for this purpose are still limited. In our research, we found that homogeneous methanolic phosphomolybdic acid (PMA) efficiently catalyzes the regioselective deprotection of 5′- O -TBS groups of a diversity of persilylated nucleoside substrates and can be applied in practical synthesis at scales of up to 15 g. 31 P NMR results indicated that an anion cluster forms and the Lewis acidity of homogeneous PMA is organic-solvent dependent. The efficacy and pronounced regioselectivity of methanolic PMA occurs as a result of a lowering of the Lewis acid strength upon solvation of the molybdophosphate anions.
A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites
Janczyk, Matthaeus,Appel, Bettina,Springstubbe, Danilo,Fritz, Hans-Joachim,Mueller, Sabine
supporting information; experimental part, p. 1510 - 1513 (2012/03/22)
Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.
cis-tetrahydrofuran-3,4-diol structure as a key skeleton of new protecting groups removable by self-cyclization under oxidative conditions
Utagawa, Eri,Sekine, Mitsuo,Seio, Kohji
, p. 7668 - 7677 (2007/10/03)
(Chemical Equation Presented) A variety of carbonate-type acyl groups having a cis-tetrahydrofuran-3,4-diol (1,4-anhydroerythritol) backbone structure and a TrS or MMTrS group have been examined as new "protected" protecting groups of the 5′-hydroxyl grou
Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'α-C-branched-chain sugar pyrimidine nucleosides
Nomura, Makoto,Shuto, Satoshi,Tanaka, Motohiro,Sasaki, Takuma,Mori, Shuichi,Shigeta, Shiro,Matsuda, Akira
, p. 2901 - 2908 (2007/10/03)
A series of 4'α-C-branched-chain pyrimidine nucleosides was synthesized from 2'-deoxycytidine or uridine. In the 2'-deoxycytidine series, the substituent at the 4'α-position affected cytotoxicity against L1210 mouse leukemic cells in vitro in the order Me (23) > CN (22)> C≡CH (21) > CH=CH2 (19) > Et (24) > CH=CHCl (20). However, uridine and cytidine derivatives with ethynyl and cyano groups at the 4'α-position did not show any cytotoxicity. The antiviral activities of these nucleosides against HSV-1, HSV-2, and HIV- 1 in vitro were also examined. Compounds 22 and 23 showed antiviral activities against HSV-1 and HSV-2 without showing significant toxicity to the host cells (MRC-5 cells). Although almost all of the nucleosides showed anti-HIV-1 activities, they were also cytotoxic to the host cells (MT-4).
Synthesis and separation of diastereoisomers of O-(2,2,2-trifluoroethyl)-3',5'-dinucleoside phosphates
Luo,Atrazheva,Fregeau,Gmeiner,Lown
, p. 1548 - 1555 (2007/10/02)
The synthesis, diastereomeric separation, and characterization are described for a series of novel O-(2,2,2-trifluoroethyl)-3',5'-dinucleoside phosphates, required for incorporation into antisense probes in the magnetic resonance imaging investigation of
Efficient procedure for the synthesis of 3'-O-t-butyldimethylsilyl-2'-deoxynucleosides
Patil, Sucheta V.,Mane, Ramchandra B.,Salunkhe, Manikrao M.
, p. 1 - 2 (2007/10/02)
3'-O-t-Butyldimethylsilyl-2'-deoxynucleosides (3) have been synthesized in high yields by the reaction of 5'-O-DMT-2'-deoxynucleosides (1) with t-butyldimethylsilyl chloride (TBDMS-Cl) in THF using butyllithium followed by detritylation with 80percent aq.
The synthesis of modified achiral internucleoside linkages: -NHCH2CH2-linked oligonucleosides
Saha, Ashis K.,Schairer, Wayne,Waychunas, Cheryl,Prasad,Sardaro, Mark,Upso, Donald A.,Kruse, Lawrence I.
, p. 6017 - 6020 (2007/10/02)
A method for the synthesis of oligonucleosides uniformly linked by the NHCH2CH2 moiety is described. Syntheses of heterodimers and a thymidylate trimer along with relevant T and nuclease resistance data are described.
Improvements in Oligodeoxyribonucleotide Synthesis: Methyl N,N-Dialkylphosphoramidite Dimer Units for Solid Support Phosphite Methodology
Kumar, G.,Poonian, M.S.
, p. 4905 - 4912 (2007/10/02)
Two procedures for the synthesis of methyl N,N-dialkylphosphoramidite dinucleotides (dimer units) compatible with the current solid support phosphite methodology of oligodeoxynucleotide synthesis are described for the first time.In the first procedure a c
