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

HRID 2372148
ノート
印刷プレビュー

反応式

HRID 2372148 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-075598ebd05e4193a185cc2842501696
出典データセット
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05097023

反応ノート

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