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

HRID 1009150노트

반응식

HRID 1009150 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 24477Sodium Thiosulfate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3245ec15d03b4e61a99cb1e57e170cb8
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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