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

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

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.

Авторлар туралы

M. Khalikova

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

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

U. Roziqov

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

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

A. Skrylkova

St. Petersburg State Institute of Technology (Technical University)

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

D. Egorov

St. Petersburg State Institute of Technology (Technical University)

Хат алмасуға жауапты Автор.
Email: diavoly@mail.ru
ORCID iD: 0000-0003-3744-9306
Ресей, Moskovskii prosp., 26, St. Petersburg, 190013

S. Safarov

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

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

Әдебиет тізімі

  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.

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML

© Russian Academy of Sciences, 2024