| Identification | More | [Name]
2,2'-Anhydro-5-methyluridine | [CAS]
22423-26-3 | [Synonyms]
2,2'-Anhydro-11-beta-D-arabinofuranosylthymine
2,2'-anhydro-1-beta-arabinofuranosylthymine
2,2'-ANHYDRO-(1-BETA-D-ARABINOFURANOSYL)THYMINE
2,2'-ANHYDRO-(1-E-D-ARABINOFURANOSYL)-5-METHYLURACIL
2,2'-ANHYDRO-5-METHYLURIDINE
2,2'-ANHYDROTHYMIDINE
(2r-(2alpha,3beta,3abeta,9abeta))-2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-6h-furo(2',3':4,5)oxazolo(3,2-a)pyrimidin-6-one
6H-FURO[2',3':4,5]OXAZOLO[3,2-A]PYRIMIDIN-6-ONE,2,3,3A,9A-TETRAHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-7-METHYL-, (2R,3R,3AS, 9AR)-
2,2'-cyclo-5-methyluridine
2,2'-Anhydrothimidine
Uridine,2,2'-cyclo-5-methyl
2,2'-Anhydro-D-thymidine
2,2’-Cryclo-5-methyluridine
2,2''-Anhydro-(1-beta-D-arabinofuranosyl)-5-methyluracil
6H-Furo[2'',3'':4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R,3R,3aS, 9aR)-
(2R-(2alpha,3beta,3abeta,9abeta))-2,3,3a,9a-Tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-6H-furo(2',3':4,5)oxazolo(3,2-a)pyrimidin-6-one
(2R)-2,3,3aβ,9aβ-Tetrahydro-3β-hydroxy-2α-(hydroxymethyl)-7-methyl-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
(8R,10R,11R,12S)-5-Methyl-10-(hydroxymethyl)-11-hydroxy-2,7:8,12-dicyclo-1,9-dioxa-3,7-diazacyclododeca-2,5-diene-4-one
2,2'β-Oxy-2-deoxo-2,3-didehydro-2'-deoxy-5-methyluridine
2'β,2-Epoxy-2,3-didehydro-2-deoxothymidine | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C10H12N2O5 | [MDL Number]
MFCD00233555 | [Molecular Weight]
240.21 | [MOL File]
22423-26-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless solid | [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) |
| Hazard Information | Back Directory | [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 |
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