Dimethoxymethane → (3R,5S)-5-[(R)-2-Benzyloxy-1-hydroxyethyl]-3-ethyldihydrofuran-2-one

HRID 1694989ノート

反応式

HRID 1694989 の反応式
B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=[O:34].[Na+].[Na+].[CH2:51]([O:58][CH2:59]/[CH:60]=[CH:61]/[CH2:62][C@@H:63]([CH2:67][CH3:68])[C:64]([OH:66])=[O:65])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.COCOC.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(#N)C>[CH2:51]([O:58][CH2:59][C@H:60]([C@H:61]1[O:65][C:64](=[O:66])[C@H:63]([CH2:67][CH3:68])[CH2:62]1)[OH:34])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

参加物

10

反応物 6

HCID 8020DimethoxymethaneHCID 11430Potassium CarbonateHCID 13020083Ethylenediaminetetraacetic acid disodium salt2 回HCID 21225931Dodecasodium;tetraborateHCID 23707502Potassium hydroxy sulfiteHCID 66645723(2R,4E)-6-Benzyloxy-2-ethylhex-4-enoic acid

生成物 1

HCID 66645773(3R,5S)-5-[(R)-2-Benzyloxy-1-hydroxyethyl]-3-ethyldihydrofuran-2-one収率 70%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

335 ml of a solution of a sodium tetraborate buffer solution (0.05 M) in a 0.4 mM disodium ethylenediaminetetraacetate aqueous solution, 0.503 g of tetrabutylammonium bisulfate (1.48 mmol) and 8.63 g of 1,2:4,5-di-O-isopropylidene-β-D-erythro-2,3-hexodiuro-2,6-pyranose (33.4 mmol) were added to 8.30 g of (2R,4E)-6-benzyloxy-2-ethylhex-4-enoic acid obtained in Example (106b) (33.5 mmol) in a mixed solvent of acetonitrile (167 ml) and dimethoxymethane (333 ml) at room temperature, and the mixture was stirred for 10 minutes. The reaction mixture was cooled in an ice bath. Then, a solution of 28.4 g of Oxone (trade mark) (46.1 mmol) in a 0.4 mM disodium ethylenediaminetetraacetate aqueous solution (168 ml) and a solution of 26.7 g of potassium carbonate (193 mmol) in water (168 ml) were separately added dropwise over four hours. The mixture was stirred at the same temperature for one hour and then diluted with 100 ml of water, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1-1/1) to obtain 6.80 g of the title compound (total yield over two steps: 70%).

後処理

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. stirringThe mixture was stirred at the same temperature for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThen, the organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1-1/1)

出典と根拠

ORDレコード
ord-f575c2b16799405ebf679f62bf1a10e0
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

読み込み中…