Tetrahydrofuran → 3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

HRID 46203ノート

反応式

HRID 46203 の反応式
ClC1N=[N:4][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([C@H:15]3[C@H:20]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@@H:19]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:18]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[O:16]3)[CH:12]=[CH:11][C:10]=2[Cl:54])=CC=1.C([N:58](CC)[CH:59]([CH3:61])[CH3:60])(C)C.C#[C:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.O1CCC[CH2:73]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:54][C:10]1[CH:11]=[CH:12][C:13]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[CH:14][C:9]=1[CH2:8][C:5]1[N:4]=[N:58][C:59]([C:60]#[C:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:61][CH:73]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86664426HCID 86664426、化合物

生成物 1

HCID 672875763-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

実験手順

To a mixture of Intermediate 6 (compound 24, 381 mg, 0.5 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (35 mg, 0.05 mmol) and copper(I) iodide (10 mg, 0.05 mmol) in tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.5 mmol) and phenylacethylene (0.07 mL, 0.6 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was washed with water and brine prior to drying over magnesium sulfate. Filtration through a plug of silica gel and removal of the volatiles under reduced pressure yielded titled compound as a brown solid, which was used without further purification.

後処理

  1. washAfter dilution with ethyl acetate, the organic layer was washed with water and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration
  4. customthrough a plug of silica gel and removal of the volatiles under reduced pressure

出典と根拠

ORDレコード
ord-7e8229c8b0bc405aafc93935874746f9
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

反応ノート

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