Potassium Sodium Tartrate → (2S,3S,4S,5R)-5-(Triethylsilyloxy)-3-hydroxy-2,4-dimethyloctanal

HRID 22082

反応式

HRID 22082 の反応式
[CH2:1]([Si:3]([CH2:19][CH3:20])([CH2:17][CH3:18])[O:4][C@H:5]([CH2:14][CH2:15][CH3:16])[C@@H:6]([CH3:13])[C@@H:7]1[O:12][C@:8]1([CH3:11])[CH2:9][OH:10])[CH3:2].C([Li])CCC.[I-].[I-].[Sm+2].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.O.CCOCC>[CH2:19]([Si:3]([CH2:1][CH3:2])([CH2:17][CH3:18])[O:4][C@H:5]([CH2:14][CH2:15][CH3:16])[C@@H:6]([CH3:13])[C@H:7]([OH:12])[C@H:8]([CH3:11])[CH:9]=[O:10])[CH3:20]

参加物

8

反応物 4

HCID 9357Potassium Sodium TartrateHCID 57283355(2R,3S,4S,5R)-5-(Triethylsilyloxy)-2,3-epoxy-2,4-dimethyl-1-octanolHCID 178418339ButyllithiumHCID 178506586HCID 178506586、化合物

生成物 1

HCID 57313995(2S,3S,4S,5R)-5-(Triethylsilyloxy)-3-hydroxy-2,4-dimethyloctanal

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

(2R,3S,4S,5R)-5-(Triethylsilyloxy)-2,3-epoxy-2,4-dimethyl-1-octanol (21.0 mg, 69.4 μmol) in 300 μl of THF at 0° C. was deprotonated with 1.05 eq of n-butyllithium. After 15 min, 0.1M samarium diiodide (764 μmol, 1.1 eq) was added and the reaction was allowed to warm to 25° C. over night. Then 1 ml of 1/2 saturated Rochelle's salt was added, stirred an additional 1 h, and poured onto 5 ml of Et2O and 1 ml of H2O. The layers were separated, extracted with ether (3×5 ml), washed with 5% NaHCO3 (2×1 ml), brine (1×1 ml), dried over MgSO4 and concentrated to give 31 crude.

後処理

  1. customat 0° C.
  2. customThe layers were separated
  3. extractionextracted with ether (3×5 ml)
  4. washwashed with 5% NaHCO3 (2×1 ml), brine (1×1 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-886f87c09f3e4a15999176d8eab283ce
出典データセット
uspto-grants-1995_06
特許番号
US05426206

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