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

HRID 456388노트

반응식

HRID 456388 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1049Pyridine용매

실험 절차

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 1 [Ref.: Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L., “Synthesis and Antiviral Evaluation of β-L-Xylofuranosyl Nucleosides of the Five Naturally Occurring Nucleic Acid Bases”, Journal of Heterocyclic Chemistry, October–November 1993, 30, 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 minutes. 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 2 (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.

후처리

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

출처 및 근거

ORD 기록
ord-29727ba985204fcf84056f99ed090cd4
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186700B2

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