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Sodium Azide → 1-Azido-1-deoxy-4-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol

HRID 2372148
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HRID 2372148 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C@H:11]([C@@H:20]([C@H:29]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[O:30][S:31]([CH3:34])(=[O:33])=[O:32])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)=O>CN(C)C=O>[N:1]([CH2:10][C@H:11]([C@@H:20]([C@H:29]([CH2:35][O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[O:30][S:31]([CH3:34])(=[O:33])=[O:32])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[N+:2]=[N-:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 539556741,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol

생성물 1

HCID 228428751-Azido-1-deoxy-4-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol수율 68.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of sodium azide (1.72 g, 26.4 mmol) and 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol (13.9 g, 24 mmol) in dimethylformamide (500 mL) is heated overnight at 60° C. under stirring. Dimethylformamide is evaporated under reduced pressure. The residue is dissolved in ethyl acetate and washed with water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure, yielding an oil. Flash chromatography on silica gel and elution with a 7:3 mixture of cyclohexane and ethyl acetate yield 1-azido-1-deoxy-4-O-methanesulfonyl -2,3,5-tri-O-benzyl-L-xylitol (8.6 g, 63%) as an oil.

후처리

  1. customDimethylformamide is evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customyielding an oil
  8. washFlash chromatography on silica gel and elution
  9. additionwith a 7:3 mixture of cyclohexane and ethyl acetate

출처 및 근거

ORD 기록
ord-075598ebd05e4193a185cc2842501696
출처 데이터셋
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05097023

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