Triacetoxyperiodinane → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one

HRID 1928679ノート

反応式

HRID 1928679 の反応式
[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH2:15][OH:16])[O:12][C:11](=[O:17])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:20]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:15]([OH:20])[OH:16])[O:12][C:11](=[O:17])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 10659025(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-one

生成物 1

HCID 44128178(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-one (150 mg, 0.58 mmol) and Dess-Martin periodinane (380 mg, 0.86 mmol) in CH2Cl2 (15 mL) is stirred at ambient temperature for 3 hours. The mixture is diluted with tBuMeO (20 mL), washed with saturated Na2S2O3 solution, saturated NaHCO3 solution, dried (MgSO4) and concentrated to give 139 mg (87%) of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxy methyl)tetrahydro-2H-pyran-2-one as white powder which is used in the next step without further purification.

後処理

  1. additionThe mixture is diluted with tBuMeO (20 mL)
  2. washwashed with saturated Na2S2O3 solution, saturated NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-737980fd8d834f6783214457a05b9877
出典データセット
uspto-grants-2012_05
特許番号
US08183397B2

反応ノート

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