Nucleosides. CXLIX. Novel and practical synthesis of α-monofluoro-and α,α-difluorothymidine (F-TDR and F2-TDR) Journal Article
| Authors: | Matulic-Adamic, J.; Watanabe, K. A. |
| Article Title: | Nucleosides. CXLIX. Novel and practical synthesis of α-monofluoro-and α,α-difluorothymidine (F-TDR and F2-TDR) |
| Abstract: | Di-O-tert-butyldiphenylsilyl (BDPS)-thymidine (2) was converted to 5'-di-O-BDPS-thymidine (3) by photobromination. Crude 3 was hydrolyzed to the a-hydroxythymidine derivative 4 which was oxidized with MnO2 to the 5-formyluracil nucleoside 5. Fluorination of 4 with diethylamino-sulfur trifluoride afforded the protected a-fluorothymidine 6. Similarly, 5 was converted into the a,a-difluorothymine nucleoside 7. These protected fluorothymidines (6 and 7) were deblocked by treatment with tetra-n-butylammonium fluoride to give α-fluorothymidine (8, F-TDR) and α,α-difluorothymidine (9, F2-TDR). © 1988, The Pharmaceutical Society of Japan. All rights reserved. |
| Keywords: | unclassified drug; nonhuman; antineoplastic agents; drug synthesis; chemistry; thymidine; thymidine derivative; fluorothymidine; support, u.s. gov't, p.h.s.; practical synthesis; trifluridine; 5-difluoromethyl-2'-deoxyuridine; 5-monofluoromethyl-2'-deoxy-uridine; α,α-difluorothymidine; α-monofluorothymidine |
| Journal Title: | Chemical and Pharmaceutical Bulletin |
| Volume: | 36 |
| Issue: | 4 |
| ISSN: | 0009-2363 |
| Publisher: | Pharmaceutical Society of Japan |
| Date Published: | 1988-04-25 |
| Start Page: | 1554 |
| End Page: | 1557 |
| Language: | English |
| DOI: | 10.1248/cpb.36.1554 |
| PUBMED: | 3138033 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 6 August 2020 -- Source: Scopus |
