chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).chemicallytech-1538Research ArticleCHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙStability of 3', 5'-o-(tetraisopropyldisiloxane-1,3-diyl)nucleosides in the presence of lewis acidsСтабильность 3', 5'-o-(тетраизопропилдисилоксан-1,3-диил)нуклеозидов в присутствии кислот Льюиса.КуликоваИ. В.KulikovaI. V.

младший научный сотрудник

noemail@neicon.ruМурадоваД. А.MuradovaD. A.

студент

noemail@neicon.ruМихайловС. Н.MikhailovS. N.

зав. лабораторией

noemail@neicon.ruИнститут молекулярной биологии РАН им. В.А. ЭнгельгардтаRussian Federation200828102008359398Copyright © Kulikova I.V., Muradova D.A., Mikhailov S.N., 20082008Куликова И.В., Мурадова Д.А., Михайлов С.Н.Kulikova I.V., Muradova D.A., Mikhailov S.N.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/1538

Trimethylsilyl trifluoromethanesulfonate catalyzes effective isomerization of 3',5'-O-(tetraisopropyldisiloxane1,3-diyl,TIPDS)nucleosides in 1,2-dicloroethane at 0C into 2',3'-O-TIPDS-derivatives to give 55-90% yields. On the other hand 3',5'-O-TIPDS-nucleosides except for uridine derivative 1a were found to be stable in the in the presence of tin tetrachloride and boron trifluoride etherate

Триметилсилилтрифторметансульфонат в 1,2-дихлорэтане при 00C эффективно катализирует изомеризацию 3',5'-O-(тетраизопропилдисилоксан-1,3-диил)- (или TIPDS-)нуклеозидов в 2',3'-O-TIPDS-производные с выходами 55–90%. В присутствии тетрахлорида олова и эфирата трехфтористого бора 3',5'-O-TIPDS-нуклеозиды оказались существенно более стабильны.

защитные группы нуклеозидовизомеризация3′5′-O-(тетраизопропилдисилоксан-13-диил)нуклеозидытриметилсилилтрифторметан-сульфонат.ReferencesMarkiewicz, W. T. Tetraisopropyldissiloxane-1,3-diyl, a group for simultaneous protection of 3'-and 5'-hydroxy functions of nucleosides / W. T. Markiewicz // J. Chem. Res. (S). – 1979. – P. 24–25; (M). – 1979. – P. 187–194.Markiewicz, W. T. Tetraisopropyldissiloxane-1,3-diyl, a group for simultaneous protection of 3'-and 5'-hydroxy functions of nucleosides / W. T. Markiewicz // J. Chem. Res. (S). – 1979. – P. 24–25; (M). – 1979. – P. 187–194.Markiewicz, W. T. Simultaneous protection of 3- and 5-hydroxyl groups of nucleosides. In Nucleic Acid Chemistry. Improved and New Synthetic Procedures and Techniques / W. T. Markiewicz, M. Wiewiorowski // Ed. L. B. Townsend, R. S. Tipson. J. Wiley & Sons. – New York, 1986; Part 3. – P. 229–231.Markiewicz, W. T. Simultaneous protection of 3- and 5-hydroxyl groups of nucleosides. In Nucleic Acid Chemistry. 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The authors declare that there are no conflicts of interest present.