Hydrochloric Acid → 1-(3,5-Di-O-benzyl-4-C-hydroxymethyl-beta-D-ribofuranosyl)-4-N-benzoylcytosine

HRID 1007603노트

반응식

HRID 1007603 반응식
C([O:4][C@@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@:8]([CH2:27][O:28]C(=O)C)([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@H:6]1[N:32]1[CH:47]=[CH:46][C:36]([NH:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:35][C:33]1=[O:34])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@@H:9]1[C@@:8]([CH2:27][OH:28])([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@@H:6]([N:32]2[CH:47]=[CH:46][C:36]([NH:37][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:35][C:33]2=[O:34])[C@@H:5]1[OH:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 206107811-(2-O-Acetyl-4-C-acetoxymethyl-3,5-di-O-benzyl-beta-D-ribofuranosyl)-4-N-benzoylcytosine

생성물 1

HCID 206107831-(3,5-Di-O-benzyl-4-C-hydroxymethyl-beta-D-ribofuranosyl)-4-N-benzoylcytosine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of nucleoside 54 (3.4 g, 5.3 mmol) in methanol (20 cm3) was added sodium methoxide (0.663 g, 11.66 mmol). The reaction mixture was stirred at room temperature for 10 min and then neutralised with 20% aqueous hydrochloric acid. The solvent was partly evaporated and the residue was extracted with dichloromethane (3×50 cm3). The combined organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×20 cm3) and was dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (98.5:1.5, v/v) as eluent to give compound 55 as a white solid material (1.6 g, 54%). δH (CDCl3) 9.95 (1H, br s, NH), 8.33 (1H, d, J 7.4, 6-H), 7.98 (2H, m, Bz), 7.60-7.12 (14H, m, Bn, Bz, 5-H), 6.17 (1H, d, J 1.6, 1′-H), 4.78 (1H, d, J 11.8, Bn), 4.48-4.27 (5H, m, Bn, 2′-H, 3′-H), 3.85 (1H, d, J 11.8, 5′-Ha), 3.66-3.61 (2H, m, 5′-Hb, 1″-Ha), 3.47 (1H, d, J 10.4, 1″-Hb). δC (CDCl3) 167.5, 162.31 (C-4, C═O), 155.36 (C-2), 145.34 (C-6), 137.49, 137.08, 133.09, 133.01, 128.94, 128.67, 128.48, 128.30, 128.01, 127.90, 127.80 (Bn, Bz), 96.53 (C-5), 93.97, 89.35 (C-1′, C-4′), 76.06, 75.28, 73.70, 72.76, 70.26, 62.44 (C-2′, C-3′, Bn, C-5′, C-1″). FAB-MS m/z 558 [M+H]+.

후처리

  1. customThe solvent was partly evaporated
  2. extractionthe residue was extracted with dichloromethane (3×50 cm3)
  3. washThe combined organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×20 cm3)
  4. dry with materialwas dried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-836802f13ce04fdfbdaa22480416c389
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794499B2

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