Acetone → 1-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracil

HRID 413671ノート

反応式

HRID 413671 の反応式
O.NN.C([O:7][C@H:8]1[C@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:11]([CH2:22][O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@@H:9]1[N:32]1[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]1=[O:34])(=O)C.CC(C)=O>N1C=CC=CC=1.C(O)(=O)C>[C:14]([O:13][C@@H:12]1[C@H:11]([CH2:22][O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@H:9]([N:32]2[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]2=[O:34])[C@H:8]1[OH:7])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 180AcetoneHCID 24654Hydrazine hydrate (1:1)HCID 103456211-(2-O-acetyl-3,5-di O-benzoyl-beta-L-xylofuranosyl)uracil

生成物 1

HCID 667170671-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracil収率 68%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1049Pyridine溶媒

実験手順

Hydrazine hydrate (1.4 mL, 28.7 mmol) was added to a solution of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)uracil 10 [Ref.: Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L., “Synthesis and Antiviral Evaluation of β-L-Xylofuranosyl Nucleosides of the Five Naturally Occuring Nucleic Acid Bases”, Journal of Heterocyclic Chemistry, 1993, 30 (Oct.-Nov.), 1229-1233] (4.79 g, 9.68 mmol) in pyridine (60 mL) and acetic acid (15 mL). The solution was stirred overnight at room temperature. Acetone was added (35 mL) and the mixture was stirred for 30 min. The reaction mixture was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (0-4%) in dichloromethane to give 11 (3.0 g, 68%) which was crystallized from cyclohexane/dichloromethane: mp=111-114° C.; 1H-NMR (DMSO-d6): δ 11.35 (br s, 1H, NH), 7.9-7.4 (m, 11H, 2 C6H5CO, H-6), 6.38 (d, 1H, OH-2′, JOH-2′=4.2 Hz), 5.77 (d, 1H, H-1′, J1′-2′=1.9 Hz), 5.55 (d, 1H, H-5, J5-6=8 Hz), 5.54 (dd, 1H, H-3′, J3′-2′=3.9 Hz and J3′-4′=1.8 Hz), 4.8 (m, 1H, H-4′), 4.7 (m, 2H, H-5′ and H-5″), 4.3 (m, 1H, H-2′); MS: FAB>0 (matrix GT) m/z 453 (M+H)+, 105 (C6H5CO)+; FAB<0 (matrix GT) m/z 451 (M−H)−, 121 (C6H5CO2)−, 111 (B)−; Anal. Calcd for C23H20N2O8.H2O: C, 58.09; H, 4.76; N, 5.96. Found: C, 57.71; H, 4.42; N, 5.70.

後処理

  1. stirringthe mixture was stirred for 30 min
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography [eluent

出典と根拠

ORDレコード
ord-9aeaabe0680348c3a37485cfc5fe6f04
出典データセット
uspto-grants-2003_05
特許番号
US06569837B1

反応ノート

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