Tetrabutylammonium Fluoride → HCID 67288226、化合物

HRID 46188ノート

反応式

HRID 46188 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@@H:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:23]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][O:5][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@@H:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:23]([O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][OH:5]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67287190(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

生成物 1

HCID 67288226HCID 67288226、化合物収率 98.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane (198 mmol) from Step 5 in tetrahydrofuran (500 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 594 mL, 594 mmol) and the reaction mixture stirred at ambient temperature for 2 h. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and saturated ammonium chloride solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes) to yield the title compound (130 g, 195 mmol, 98%, mixture of α,β-anomer in about 1:2 ratio) as a white solid.

後処理

  1. customAfter removal of organic volatiles under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated ammonium chloride solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-a5a33240802e4867a54fa1e428fc6e8d
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

反応ノート

読み込み中…