1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (1R,3R,4R,7R)-1-(4,4'-Dimethoxytrityloxymethyl)-7-Hydroxy-3-(Thymin-1-yl)-2,5-Dioxabicyclo[2.2.1]Heptane

HRID 6782

反応式

HRID 6782 の反応式
[OH:1][C@@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:18][OH:19])[O:4][C@H:5]2[N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11].[CH3:20][O:21][C:22]1[CH:43]=[CH:42][C:25]([C:26](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]([O:19][CH2:18][C@@:3]23[C@H:2]([OH:1])[C@@H:6]([O:7][CH2:8]2)[C@H:5]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:4]3)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:25]2[CH:42]=[CH:43][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)=[CH:32][CH:31]=1

参加物

5

反応物 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)2 回HCID 516892Sodium BicarbonateHCID 10849623(1S,3R,4R,7R)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo [2.2.1]heptane

生成物 1

HCID 15374272(1R,3R,4R,7R)-1-(4,4'-Dimethoxytrityloxymethyl)-7-Hydroxy-3-(Thymin-1-yl)-2,5-Dioxabicyclo[2.2.1]Heptane収率 50%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a stirred solution of nucleoside 9 (0.500 g, 1.85 mmol) in anhydrous pyridine (10 cm3) was added 4,4′-dimethoxytrityl chloride (0.941 g, 2.78 mmol) and the mixture was stirred for 25 h at room temperature for 25 h after which additional 4,4′-dimethoxytrityl chloride (0.062 g, 0.18 mmol) was added and stirring at room temperature was continued for another 21 h. A saturated aqueous solution of sodium hydrogen carbonate (50 cm3) was added and extraction was performed using dichloromethane (3×25 cm3). The combined organic phase was washed with saturated aqueous solutions of sodium hydrogen carbonate (3×20 cm3) and brine (3×25 cm3), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol/pyridine (1–4% methanol, 0.5% pyridine, v/v/v) as eluent to give nucleoside 10 (0.53 g, 50%) as a white solid material after evaporation of the solvents under reduced pressure (0.307 g, 28.9%).

後処理

  1. additionwas added
  2. extractionextraction
  3. washThe combined organic phase was washed with saturated aqueous solutions of sodium hydrogen carbonate (3×20 cm3) and brine (3×25 cm3)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f85f96ac167340d3b6eec326e09ec856
出典データセット
uspto-grants-2006_08
特許番号
US07084125B2

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