1-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracil → 2 inverted exclamation marka-Deoxy-|A-L-uridine

HRID 2116735Notes

Reaction equation

HRID 2116735 reaction equation
C([O:9][C@@H:10]1[C@H:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[O:13][C@H:12]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:11]1O)(=O)C1C=CC=CC=1>CO.O>[C@H:12]1([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[O:13][C@@H:14]([CH2:15][OH:16])[C@@H:10]([OH:9])[CH2:11]1

Participants

4

Reactant 1

HCID 667170671-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracil

Product 1

HCID 6879712 inverted exclamation marka-Deoxy-|A-L-uridineYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3,5-di-O-benzoyl-β-L-xylofuranosyl)-uracil (6a) (1.4 g: 3.21 mmol) in ammoniacal methanol (previously saturated at 10° C. and hermetically closed) (90 ml) is stirred for two days at room temperature. The solution is evaporated several times with methanol under reduced pressure. The crude material obtained is dissolved in water and the resulting solution is washed several times with chloroform. The aqueous phase is evaporated and the residue is directly crystallized from methanol to give 0.6 g (yield 82%) of pure 7a: m.p.: 165-167° C.; 1H NMR (DMSO-d6), δ ppm=11.23 (s, 1H, 3-NH), 7.92 (d, 1H H-6; J=8.1 Hz), 6.04 (dd, 1H, H-1′; J=2.0 and 8.3 Hz), 5.26 (d, H, H-5; J=8.1 Hz), 5.26 (d, 1H, OH-3′; J=3.2 Hz), 4.69 (t, 1H, OH-5′; J=5.3 Hz), 4.20 (m, 1H, H-3′), 3.81 (m, 1H, H-4′), 3.80-3.60 (m, 2H, H-5′ and 5″), 2.6-2.5 (m, 1H, H-2′, partially obscured by DMSO-d5), 1.85 (dd, 1H, H-2″; J=2.0 and 14.7 Hz); mass spectra (matrix: glycerol-thioglycerol: 50:50, v/v): FAB>0 321 [M+glycerol+H]+, 229 [M+H]+, 117 [s]+ and 113 [BH2]+; FAB<0 227 [M−H]−.

Workup

  1. customThe solution is evaporated several times with methanol under reduced pressure
  2. customThe crude material obtained
  3. washthe resulting solution is washed several times with chloroform
  4. customThe aqueous phase is evaporated
  5. customthe residue is directly crystallized from methanol

Sources & evidence

ORD record
ord-7a0698e16e594469a217339a02a0c9b4
Source dataset
uspto-grants-2008_10
Patent number
US07439351B2

Reaction notes

Loading…