Synthesis of (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The article presents a method for the preparation of (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside from (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-L-talofuranoside by successive treatment of the latter with a 20% solution of hydrochloric acid in aqueous methanol, followed by treatment with benzoyl chloride in dry pyridine. A promising use of methyl (1S,2S,3R,4R,5S)-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside for the synthesis of new modified nucleosides after its acetylation has also been shown.

About the authors

M. J. Khalikova

V. I. Nikitin Institute of Chemistry, National Academy of Sciences of Tajikistan

Email: diavoly@mail.ru
Tajikistan, ul. Ayni, 299/2, Dushanbe, 734063

U. A. Roziqov

V. I. Nikitin Institute of Chemistry, National Academy of Sciences of Tajikistan

Email: diavoly@mail.ru
Tajikistan, ul. Ayni, 299/2, Dushanbe, 734063

A. S. Skrylkova

St. Petersburg State Institute of Technology (Technical University)

Email: diavoly@mail.ru
Russian Federation, Moskovskii prosp., 26, St. Petersburg, 190013

D. M. Egorov

St. Petersburg State Institute of Technology (Technical University)

Author for correspondence.
Email: diavoly@mail.ru
ORCID iD: 0000-0003-3744-9306
Russian Federation, Moskovskii prosp., 26, St. Petersburg, 190013

S. Sh. Safarov

V. I. Nikitin Institute of Chemistry, National Academy of Sciences of Tajikistan

Email: diavoly@mail.ru
ORCID iD: 0000-0002-7193-6135
Tajikistan, ul. Ayni, 299/2, Dushanbe, 734063

References

  1. Fischer E., Piloty O. Ber. Dtsch. Chem. Ges. 1891, 24, 4214–4225. doi: 10.1002/cber.189102402322
  2. Eugenio F., Lourdes R. J. Biol. Chem. 2019, 294, 2249–2255. doi: 10.1074/jbc.CL119.007397.
  3. Jeanloz R.W., Fletcher H. G. Adv. Carbohydr. Chem. 1951, 6, 135–174. doi: 10.1016/S0096–5332(08)60066–1.
  4. Mao-Chin L., Mei-Zhen L., Diane E. M., Alan C. S. Nucleosid. Nucleotid. Nucleic. Acids. 2005, 24, 45–62. doi: 10.1081/NCN-46784.
  5. Hassan A.E.A., Abou-Elkhair R.A.I., Parker W. B., Allan P. W., Secrist III J. A. Bioorg. Chem. 2016, 65, 9–16. doi: 10.1016/j.bioorg.2015.12.006.
  6. Chhikara B.S., Parang K. Expert Opin. Drug Deliv. 2010, 7, 1399–1414. doi: 10.1517/17425247.2010.527330.
  7. Li Y., Li P., Li Y., Zhang R., Yu P., Ma Z., Kainov D. E., de Man R. A., Peppelenbosch M. P., Pan Q. Antivir. Res. 2020, 184, 104967. doi: 10.1016/j.antiviral.2020.104967.
  8. Cihák A. Oncology. 1974, 30, 405–422. doi 10.1159/ 000224981.
  9. Liliemark J. Clin. Pharmacokinet. 1997, 32, 120–131. doi: 10.2165/00003088–199732020–00003.
  10. Kantarjian H.M., O′Brien S., Cortes J., Giles F. J., Faderl S., Issa J. P., Garcia-Manero G., Rios M. B., Shan J., Andreeff M., Keating M., Talpaz M. Cancer. 2003, 98, 522–528. doi: 10.1002/cncr.11543.
  11. Allen-Mersh T.G., Earlam S., Fordy C., Abrams K., Houghton J. Lancet. 1994, 344, 1255–1260. doi: 10.1016/S0140–6736(94)90750–1.
  12. Tournilhac O., Cazin B., Leprètre S., Diviné M., Maloum K., Delmer A., Grosbois B., Feugier P., Maloisel F., Villard F., Villemagne B., Bastit D., Belhadj K., Azar N., Michallet M., Manhès G., Travade P. Blood. 2004, 103, 363–365. doi: 10.1182/blood-2003–05–1449.
  13. http://www.cancer.gov/cancertopics/druginfo/fda-nelarabine; Архивная копия от 11 сентября 2014 на Wayback Machine FDA Approval for Nelarabine.
  14. Wangsomboonsiri W., Mahasirimongkol S., Chantarangsu S., Kiertiburanakul S., Charoenyingwattana A., Komindr S., Thongnak C., Mushiroda T., Nakamura Y., Chantratita W., Sungkanuparph S. Clin. Infect. Dis 2010, 50, 597–604. doi: 10.1086/650003.
  15. Lai C.L., Leung N., Teo E. K., Tong M., Wong F., Hann H. W., Han S., Poynard T., Myers M., Chao G., Lloyd D., Brown N. A. Gastroenterology. 2005, 129, 528–536. doi: 10.1016/j.gastro.2005.05.053.
  16. Wilhelmus K.R. Cochrane Database Syst Rev. 2015, 1, CD002898. doi: 10.1002/14651858.CD002898.pub5
  17. Ko W.C., Rolain J. M., Lee N. Y., Chen P. L., Huang C. T., Lee P. I., Hsueh P. R. Int. J. Antimicrob. Agents. 2020, 55, 105933. doi: 10.1016/j.ijantimicag.2020.105933.
  18. Hassan A.E.A., Abou-Elkhair R.A.I., Parker W. B., Allan P. W., Secrist III J. A. Eur. J. Med. Chem. 2016, 108, 616–622. doi: 10.1016/j.ejmech.2015.12.029.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2024 Russian Academy of Sciences