The nucleoside derivative N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxy carbonyl-guanosine (compound 1) was obtained by selectively cleaving the 1,1,3,3-tetraisopropyldisiloxanyl protecting group at 5'-position with pyridinium hydrofluoride. Liquid chromatography-mass spectrometry (LC-MS), gas chromatography-high resolution mass spectrometry (GC-HRMS), liquid one-dimensional/two-dimensional nuclear magnetic resonance (NMR) techniques (i.e., 1H NMR, 13C NMR, 19F NMR, DEPT, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC) were used to assign the signals.
WEI Hui-qiang
,
YU Jiang
,
BI Chang-fen
,
NING Hong-xin
,
LI Yi-liang
,
LIU Qiang
. An NMR Study of N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxycarbonyl-guanosine[J]. Chinese Journal of Magnetic Resonance, 2019
, 36(1)
: 93
-102
.
DOI: 10.11938/cjmr20182666
[1] MARKIEWICZ W, PADYUKOVA N, SAMEK Z, et al. The reaction of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane with cytosine arabinoside and 1-(6-deoxy-α-L-talofuranosyl)uracil[J]. Collect Czech Chem Commun, 1980, 45(6):1860-1865.
[2] KARPEISKY A, GONZALEZ C, BURGIN A, et al. Highly efficient synthesis of 2'-O-amino nucleosides and their incorporation in hammerhead ribozymes[J]. Tetrahedron Lett, 1998, 39(10):1131-1134.
[3] NISHIZONO N, SUMITA Y, UENO Y, et al. Effects of 2'-O-(trifluoromethyl)adenosine on oligodeoxynucleotide hybridization and nuclease stability[J]. Nucleic Acids Res, 1998, 26(22):5067-5072.
[4] HANESSIAN S, MACROTTE S, MAHARANI R, et al. Total synthesis of malayamycin A and analogues[J]. Tetrahedron, 2006, 62(22):5201-5214.
[5] ZHU X F, WILLIAMS H, SCOTT I. Aqueous trifluoroacetic acid-an efficient reagent for exclusively cleaving the 5'-end of 3',5'-TIPDS protected ribonucleosides[J]. Tetrahedron Lett, 2000, 41(56):9541-9545.
[6] WU Q P, CHEN W, WANG Y, et al. Mild, efficient and highly selective hydrolysis of acetonides with antimony trichloride[J]. Lett Org Chem, 2006, 3(4):271-274.
[7] ZHOU Z G, YUAN Y Y, LIU H B, et al. An NMR study on prucalopride[J]. Chinese J Magn Reson, 2018, 35(1):119-127. 周中高, 元洋洋, 刘红波, 等. 普卡必利的NMR研究[J]. 波谱学杂志, 2018, 35(1):119-127.
[8] SUN W, SHE M Y, ZONG C L, et al. An NMR study on diacetonefructose[J]. Chinese J Magn Reson, 2017, 34(3):329-337. 孙伟, 厍梦尧, 宗春蕾, 等. 果糖二丙酮的结构全归属[J]. 波谱学杂志, 2017, 34(3):329-337.
[9] TIMOSHCHUK V, HOGREFE R, VAGHEFI M. Improved and reliable synthesis of 3'-azido-2',3'-dideoxyguanosine derivatives[J]. Nucleosides, Nucleotides and Nucleic Acids, 2004, 23(1-2):171-181.
[10] 张正行. 有机光谱分析[M]. 北京:人民卫生出版社, 2009.
