Pyridine → HCID 11802677、化合物

HRID 1827445

反応式

HRID 1827445 の反応式
[CH2:1]([O:8][C@H:9]1[C:13]([CH2:16][OH:17])([CH2:14][OH:15])[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@@H:10]1[OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:34][O:35][C:36]1[CH:57]=[CH:56][C:39]([C:40](Cl)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)=[CH:38][CH:37]=1>O1CCCC1.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:8][C@H:9]1[C@@:13]([CH2:14][O:15][C:40]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[C:39]2[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:57][CH:56]=2)([CH2:16][OH:17])[O:12][C@@H:11]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@@H:10]1[OH:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 106910381-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

生成物 1

HCID 11802677HCID 11802677、化合物収率 32.4%

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of nucleoside 1-(3-O-Benzyl-4-C-hydroxymethyl-β-D-xylofuranosyl)thymine 5 (5.38 g, 14.2 mmol) in anhydrous tetrahydrofuran (400 cm3) was added AgNO3 (2.66 g, 15.7 mmol) followed by anhydrous pyridine (5.7 cm3) and 4,4′-dimethoxytrityl chloride (5.30 g, 15.6 mmol). The mixture was stirred in the dark under nitrogen for 18 h at room temperature. The reaction was quenched by addition of a saturated aqueous solution of sodium hydrogen carbonate (10 cm3) and the resulting mixture was extracted with dichloromethane. The combined organic phase was evaporated to dryness under reduced pressure and the residue was co-evaporated with toluene and was purified by silica gel column chromatography using dichloromethane/methanol/pyridine (0.5% methanol; 0.5% pyridine, v/v) as eluent to afford nucleoside 6 (3.13 g, 31%) as a white foam after evaporation of the solvents. δC ((CD3)2SO) 164.1 (C-4), 158.4, 145.1, 138.5, 137.0, 135.9, 135.7, 130.1, 130.1, 129.2, 128.5, 128.5, 128.2, 128.1, 127.7, 127.6, 127.0, 125.7, 113.5 (DMT, benzyl, C-6), 151.4 (C-2), 110.1 (C-5), 85.8, 85.2, 84.6, 83.5 (C-1′, C-3′, C-4′, DMT), 76.8 (C-2′), 72.3 (CH2Ph), 65.2 (C-5″), 62.1 (C-5′), 55.4 (2× CH3O), 12.6 (5-CH3).

後処理

  1. customThe reaction was quenched by addition of a saturated aqueous solution of sodium hydrogen carbonate (10 cm3)
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. customThe combined organic phase was evaporated to dryness under reduced pressure
  4. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9ad7bca34f524919895107b140cb56ac
出典データセット
uspto-grants-2006_05
特許番号
US07053207B2

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