2,2'-Anhydro-5-methyluridine Chemical Properties

Melting point:

217.0 to 221.0 °C

Boiling point:

452.0±55.0 °C(Predicted)

Density 

1.88±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

pka

12.56±0.60(Predicted)

color 

White to Almost white

InChI

InChI=1S/C10H12N2O5/c1-4-2-12-9-7(6(14)5(3-13)16-9)17-10(12)11-8(4)15/h2,5-7,9,13-14H,3H2,1H3/t5-,6-,7+,9-/m1/s1

InChIKey

WLLOAUCNUMYOQI-JAGXHNFQSA-N

SMILES

C12O[C@@]3([H])[C@H](O)[C@@H](CO)O[C@@]3([H])N1C=C(C)C(=O)N=2

CAS DataBase Reference

22423-26-3(CAS DataBase Reference)

Safety Information

HS Code 

2940.00.6000

2,2'-Anhydro-5-methyluridine Usage And Synthesis

Chemical Properties

Colourless solid

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

2,2'-Anhydro-5-methyluridine(22423-26-3)Related Product Information

• Tiglic aldehyde
• CHLOROPHOSPHONAZO III
• 2,4-Dimethyl aniline
• Doxifluridine
• 5-Methyluridine
• 2,6-Lutidine
• Trifluridine
• L-Uridine
• Uridine
• uridine diphosphate glucose {= UDP-glucose}
• 4-Hydroxypyrimidine
• 2,2'-Cyclouridine
• 4(1H)-Pyrimidinone, 2-methoxy- (9CI)
• 2,2'-Anhydro-5-methyluridine