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

HRID 2116735노트

반응식

HRID 2116735 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-7a0698e16e594469a217339a02a0c9b4
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439351B2

반응 노트

불러오는 중…