Dimethylformamide → HCID 21362959, 화합물

HRID 1169011노트

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HRID 1169011 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[CH3:25][S:26](=[S:29])([O-:28])=[O:27].[Na+].CN(C=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:25][S:26](=[S:29])([O:28][C@@H:6]1[O:7][C@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])=[O:27]

참가 물질

7

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HCID 6228DimethylformamideHCID 24436Sodium SulfateHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate2회HCID 23688755Methanesulfonothioic acid, sodium salt

생성물 1

HCID 21362959HCID 21362959, 화합물수율 75%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매2회

실험 절차

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide (1 g, 2.44 mmol) and sodium methanethiosulfonate (0.4 g, 3.05 mmol) were placed under nitrogen. 30 ml of anhydrous toluene was added followed by tetrabutylammonium bromide (69 mg, 0.21 mmol) and the mixture heated under reflux for 75 minutes. Part way through 6 ml of DMF were added as it seemed that 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide was insoluble in toluene. Reaction continued to reflux despite the fact that solution not formed. Thin Layer Chromatography (“TLC”) at end of reaction showed reaction to have gone to completion. Solution reduced on high pressure rotary evaporator to remove DMF. Product purified on flash silica gel column, reaction mixture added directly onto column (adding a small amount of Celite to reaction mixture sufficient to avoid salt cake forming on top of column.) Petroleum Ether: Ethyl Acetate 60:40 was used as the eluting solvent. Yield=75%.

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 75 minutes
  3. customReaction
  4. temperatureto reflux despite the fact that solution not
  5. customformed
  6. customThin Layer Chromatography (“TLC”) at end of reaction
  7. customreaction
  8. customSolution reduced on high pressure rotary evaporator
  9. customto remove DMF
  10. customProduct purified on flash silica gel column, reaction mixture
  11. additionadded directly onto column (
  12. additionadding a small amount of Celite
  13. customto reaction mixture sufficient

출처 및 근거

ORD 기록
ord-c5aa2762da0e4d8f9bba42fcb7424456
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627744B2

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