Dichloromethane → (1R,3R,4R,7R)-7-Benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-3-(Thymin-1-yl)-2,5-Dioxabicyclo[2.2.1]Heptane

HRID 6780

反応式

HRID 6780 の反応式
[CH2:1]([O:8][C@H:9]1[C@@:13]([CH2:39]OS(C2C=CC(C)=CC=2)(=O)=O)([CH2:14][O:15][C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:51]2[CH:59]=[C:57]([CH3:58])[C:55](=[O:56])[NH:54][C:52]2=[O:53])[C@@H:10]1[OH:60])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(=O)([O-])O.[Na+].ClCCl>CN(C=O)C.ClCCl.N1C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@H:10]2[O:60][CH2:39][C@:13]1([CH2:14][O:15][C:16]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[O:12][C@H:11]2[N:51]1[CH:59]=[C:57]([CH3:58])[C:55](=[O:56])[NH:54][C:52]1=[O:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 106530721-(3-O-Benzyl-5-O-(4,4'-dimethoxytrityl)-4-C-(p-toluenesulphonyloxymethyl)-beta-D-Xylofuranosyl)thymine

生成物 1

HCID 10675873(1R,3R,4R,7R)-7-Benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-3-(Thymin-1-yl)-2,5-Dioxabicyclo[2.2.1]Heptane収率 96%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21875418Pyridine methylene chloride溶媒

実験手順

To a solution of nucleoside 7 (4.22 g, 5.06 mmol) in anhydrous DMF (25 cm3) at 0° C. was added a 60% suspension of sodium hydride in mineral oil (w/w, 0.607 g, 1 5.7 mmol, added in four portions during 20 min) and the reaction mixture was stirred at room temperature for 25 h, cooled to 0° C. and diluted with dichloromethane/pyridine (100 cm3, 99.5:0.5, v/v). A saturated aqueous solution of sodium hydrogen carbonate (120 cm3) was added whereupon extraction was performed using dichloromethane (75 cm3×2). The combined organic phase was washed with saturated aqueous solutions of sodium hydrogen carbonate (60 cm3×3) and brine (40 cm3×3), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol/pyridine (0.5–1.5% methanol; 0.5% pyridine, v/v/v) as eluent yielding nucleoside 8 (3.2 g, 96%) as a white solid material after evaporation of the solvents under reduced pressure.

後処理

  1. temperaturecooled to 0° C.
  2. washThe combined organic phase was washed with saturated aqueous solutions of sodium hydrogen carbonate (60 cm3×3) and brine (40 cm3×3)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4a56ae67280a44f09cf792935a32deac
出典データセット
uspto-grants-2006_08
特許番号
US07084125B2

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