93134-40-8Relevant academic research and scientific papers
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 new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites
Janczyk, Matthaeus,Appel, Bettina,Springstubbe, Danilo,Fritz, Hans-Joachim,Mueller, Sabine
, 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.
Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides
Radi, Marco,Spinosa, Raffaella,Parlato, Maria Cristina,Corelli, Federico,Botta, Maurizio
, p. 151 - 166 (2008/02/09)
In the present work the synthesis of building blocks (2a,b), bearing a masked form of the reactive vinyl group bound to the C-6 position of a cytidine derivative, has been studied. The understanding of byproduct formation together with conformational considerations let us to plan a straightforward approach for the synthesis of the target compounds.
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.
Silylation of 5'-O-DMT-2'-deoxynucleosides using dibenzo [18] crown-6-and PTC
Kore,Patil,Salunkhe
, p. 2599 - 2603 (2007/10/02)
3'-O-silylated derivatives of 5'-O-DMT-2'-deoxynucleoside (2) were synthesized in high yield by reaction of 5'-O-DMT-2'-deoxynucleosides (1) with tert-butyl dimethylsilylchloride using sodium hydride, benzyltriethylammonium chloride [TEBA] and a catalytic
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
