1006364-60-8Relevant articles and documents
Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar
Ishii, Kazuki,Saito-Tarashima, Noriko,Ota, Masashi,Yamamoto, Seigi,Okamoto, Yasuko,Tanaka, Yoshiyuki,Minakawa, Noriaki
, p. 6589 - 6594 (2016/09/23)
The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.
New RNA purine building blocks, 4'-selenopurine nucleosides: First synthesis and unusual mixture of sugar puckerings
Yu, Jinha,Kim, Jin-Hee,Lee, Hyuk Woo,Alexander, Varughese,Ahn, Hee-Chul,Choi, Won Jun,Choi, Jungwon,Jeong, Lak Shin
, p. 5528 - 5532 (2013/06/04)
Writer's blocks: The first synthesis of RNA purine building blocks, 4'-selenoadenosine and 4'-selenoguanosine was achieved from D-ribose by regioisomeric rearrangement, which was confirmed by X-ray crystallography. 4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state.
Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides
Tosh, Dilip K.,Won, Jun Choi,Hea, Ok Kim,Lee, Yoonji,Pal, Shantanu,Hou, Xiyan,Choi, Jungwon,Choi, Sun,Lak, Shin Jeong
, p. 4259 - 4262 (2008/09/20)
(Chemical Equation Presented) Stereoselective synthesis of novel 2′,3′-didehydro-2′,3′-dideoxy-4′- selenonucleosides (4′-seleno-d4Ns) 4a-c was accomplished via 4′-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4′-Selenoribofuranosyl pyrimidi