Uses
2,2'-Anhydro-5-methyluridine serves as a precursor to synthesize 5'-O-(4,4'-dimethoxytrityl)-2,2'-anhydro thymidine by reaction with 4,4'-dimethoxytrityl chloride in anhydrous pyridine[6].
Synthesis
The following is the general procedure for the synthesis of (2R,3R,3aS,9aR)-3-hydroxy-2-(hydroxymethyl)-7-methyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one from 5-methyluridine:
1. reaction catalyzed by diphenyl carbonate and NaHCO3 in DMF at 100 °C in 90% yield.
2. reaction using DMTCl in pyridine at room temperature in 89% yield.
3. reaction catalyzed by ethylene glycol, Ti(OiPr)4 and NaHCO3 in THF at 150 °C in 79% yield.
4. reaction with MsCl and Et3N in DCM in 57% yield.
5. reaction using NaN3 and 18-crown-6 in DMF in 89% yield.
6. reaction in THF with Ph3P and H2O in 89% yield.
7. reaction in DCM and Et3N in 88% yield.
8. finally, reaction with (iPr)2NP(Cl)OCH2CH2CN and DIPEA in DCM at room temperature in 59.4% yield.
References
[1] Patent: CN103450302, 2016, B. Location in patent: Paragraph 0096-0098; 0110
[2] Patent: US2013/231473, 2013, A1. Location in patent: Paragraph 0158
[3] Patent: US2005/107324, 2005, A1. Location in patent: Page/Page column 26
[4] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 4, p. 816 - 821
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1641 - 1652
