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

HRID 2100274ノート

反応式

HRID 2100274 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-7654b8d8b56e42f3a8b382966c5a45fc
出典データセット
uspto-grants-2009_08
特許番号
US07572582B2

反応ノート

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