Triacetoxyperiodinane → Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

HRID 20045ノート

反応式

HRID 20045 の反応式
[CH2:1]([O:4][CH2:5][C@H:6]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@H:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][OH:9])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[CH2:1]([O:4][CH2:5][C@H:6]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@H:7]([O:10][Si:11]([C:14]([CH3:16])([CH3:17])[CH3:15])([CH3:12])[CH3:13])[CH:8]=[O:9])[CH:2]=[CH2:3]

参加物

7

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 86614136Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-ylcarbamate

生成物 1

HCID 86614135Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

試薬・触媒・溶媒 4

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 24477Sodium Thiosulfate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

The crude material from Step 4 (0.040 g) was dissolved in CH2Cl2 (3 mL) and treated with Dess-Martin periodinane (0.07 g, 0.2 mmol). The mixture was stirred at ambient temperature for 4 h then diluted with EtOAc (10 mL), sat'd NaHCO3 (5 mL), and aqueous Na2S2O3 (5 mL). The biphasic mixture was stirred until it was colorless. The organic layer was washed with brine, dried (Na2SO4), filtered, and conc in vacuo. The crude aldehyde was used without further purification.

後処理

  1. stirringThe biphasic mixture was stirred until it
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe crude aldehyde was used without further purification

出典と根拠

ORDレコード
ord-b4ede3342f58419b9e8e391148d5fd35
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

反応ノート

読み込み中…