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Triethylamine → 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol

HRID 2372147
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인쇄 미리보기

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HRID 2372147 반응식
[CH2:1]([O:8][C@@H:9]([C@@H:12]([C@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([O:11][CH2:10][C@H:9]([C@@H:12]([C@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:22][S:40]([CH3:39])(=[O:42])=[O:41])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:42])=[O:41]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 541141622,3,5-tri-O-benzyl-L-xylitol

생성물 1

HCID 539556741,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol수율 99.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-10 °C

실험 절차

2,3,5-Tri-O-benzyl-L-xylitol (10.2 g, 24.17 nmmol) is dissolved in dry methylene chloride (100 ml) containing triethylamine (10.1 mL, 72.5 mmol). The mixture is cooled to -10° C. and methane sulfonylchloride (3.93 mL, 50.75 mmol) is added dropwise. The mixture is stirred 30 minutes at -10° C. and washed with water. The organic layer is dried over sodium sulfate, filtered and put to dryness under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a 4:6 mixture of ethyl acetate and cyclohexane yield 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-L-xylitol as an oil (13.9 g, 99%).

후처리

  1. washwashed with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. customto afford an oil
  5. washFlash chromatography on silica gel and elution
  6. additionwith a 4:6 mixture of ethyl acetate and cyclohexane

출처 및 근거

ORD 기록
ord-797587459d4f4eaa92ebf509c53f122b
출처 데이터셋
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05097023

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