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

HRID 2116735ノート

反応式

HRID 2116735 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-7a0698e16e594469a217339a02a0c9b4
出典データセット
uspto-grants-2008_10
特許番号
US07439351B2

反応ノート

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