(2S,3R,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol → 1,5 anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose

HRID 1648804ノート

反応式

HRID 1648804 の反応式
[CH3:1][C@@H:2]1[O:7][CH:6]=[CH:5][C@H:4]([OH:8])[C@H:3]1[OH:9]>C1C=CC=CC=1.C([O-])([O-])=O.[Ag+].[Ag+]>[CH:6]1[O:7][C@@H:2]([CH3:1])[C@H:3]([OH:9])[C:4](=[O:8])[CH:5]=1

参加物

4

反応物 1

HCID 10986248(2S,3R,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol2 回

生成物 1

HCID 109424341,5 anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose

試薬・触媒・溶媒 2

HCID 92796Silver carbonate触媒2 回HCID 241Benzene溶媒

実験手順

When Fetizon's reagent is used, L-rhamnal is dissolved in benzene and then the Fetizon's reagent is added to the mixture (20 g reagent: 1 g L-rhamnal). The mixture is refluxed for 1 hour, the spent reagent removed by filtration, and the solvent removed by evaporation to yield nearly pure enone. When the oxidant is chromium trioxide:pyridine complex, L-rhamnal is added to a solution of the oxidant in dichloromethane followed by addition of 4 equivalents of acetic anhydride. After 20 minutes the reaction mixture is poured onto a column of silica gel (ethyl acetate eluent) containing excess ethyl acetate at the top to precipitate insoluble chromium compounds. The product is eluted with ethyl acetate. If manganese dioxide is used, L-rhamnal is dissolved in tetrahydrofuran and treated with active manganese dioxide (15 g MnO2 : 1 g L-rhamnal) and stirred at room temperature for 2-3 days. The oxidant is then removed by filtration and the product purified by chromatography on a silica gel column (ethyl acetate eluent).

後処理

  1. temperatureThe mixture is refluxed for 1 hour
  2. customthe spent reagent removed by filtration
  3. customthe solvent removed by evaporation

出典と根拠

ORDレコード
ord-a88d6a35e59946c299bc2ba98c5d0ba4
出典データセット
uspto-grants-1983_11
特許番号
US04413120

反応ノート

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