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Potassium Iodide → (2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

HRID 1510174
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HRID 1510174 반응식
[S:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[I-].[K+]>CN(C=O)C.O.CCOCC>[CH2:21]([O:4][C@@H:3]1[C@@H:5]([O:6][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:7]([O:8][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:9]([CH2:11][O:12][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:10][C@H:2]1[S:1][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2802071phenyl thio-beta-D-galactopyranoside

생성물 1

HCID 11104159(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran수율 60.3%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

실험 절차

To the crude 9 (72.1 mmol, 1 eq) dissolved in dry DMF (1500 mL) under argon at 0° C. was added sodium hydride (10.7 g, 446.8 mmol, 6.2 eq). After 15 min, were added dropwise benzyl bromide (54 mL, 454 mmol, 6.3 eq) and a catalytic amount of potassium iodide. The mixture was stirred at room temperature for 3 h, diluted with water (500 mL) and Et2O (600 mL). The aqueous phase was extracted with Et2O (3×300 mL). The organic extracts were combined, dried over MgSO4 and concentrated. Purification by flash chromatography on silica gel (petroleum ether/EtOAc 90:10) afforded 10 as viscous syrup (27.5 g, 60% over 2 steps).

후처리

  1. extractionThe aqueous phase was extracted with Et2O (3×300 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (petroleum ether/EtOAc 90:10)

출처 및 근거

ORD 기록
ord-b44eed2963d74751a600727988025e9b
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08211859B2

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