Tetrabutylammonium Fluoride → HCID 67288226、化合物

HRID 2042906ノート

反応式

HRID 2042906 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>C1COCC1>[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%

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-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane in THF (500 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 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 EtOAc and saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified on column chromatography to provide the titled compound (168 g, 98%, ca. 2:1 mixture of anomers (β:α)) as a white solid.

後処理

  1. customAfter removal of organic volatiles under reduced pressure
  2. customthe residue was partitioned between EtOAc and saturated ammonium chloride
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on column chromatography

出典と根拠

ORDレコード
ord-f89d59cf798e4ff1928df6e8177c816d
出典データセット
uspto-grants-2013_11
特許番号
US08586550B2

反応ノート

読み込み中…