Sodium Thiosulfate → 2,6-Anhydro-5-azido-1-O-[tert-butyl(dimethyl)silyl]-4,5-dideoxy-L-erythro-hex-3-ulose

HRID 470705노트

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HRID 470705 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]([C@@H:26]1[CH2:31][C@H:30]([OH:32])[C@@H:29]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[O:28][CH2:27]1)=[N+:24]=[N-:25].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[N:23]([C@H:26]1[CH2:27][O:28][C@H:29]([CH2:33][O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36])[C:30](=[O:32])[CH2:31]1)=[N+:24]=[N-:25]

참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 866726081,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol

생성물 1

HCID 866726102,6-Anhydro-5-azido-1-O-[tert-butyl(dimethyl)silyl]-4,5-dideoxy-L-erythro-hex-3-ulose수율 76.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A Dess-Martin reagent (876 mg, 2.00 mmol) was added to a dichloromethane (10 ml) solution of 1,5-anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol (450 mg, 1.25 mmol) under ice cooling and the resulting mixture was stirred for 75 minutes. Aqueous sodium thiosulfate solution was added under ice cooling, then the resulting mixture was subjected to extraction with ether and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=50:1→20:1 (v/v)] to give 272 mg (76%) of the title compound as a colorless oil.

후처리

  1. extractionthe resulting mixture was subjected to extraction with ether
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=50:1→20:1 (v/v)]

출처 및 근거

ORD 기록
ord-7d4a8841c37049cb857eea5164869265
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629133B2

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