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N-bromobutanimide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

HRID 1510175
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HRID 1510175 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][C@H:10]1SC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:53])CC)C.BrN1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][C@@H:10]1[F:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 67184N-bromobutanimideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11104159(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

생성물 1

HCID 99590292,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride수율 73.4%

시약·촉매·용매

1
HCID 6344Dichloromethane용매2회

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온도
-15 °C

실험 절차

To a solution of 10 (10.0 g, 15.82 mmol, 1 eq) in dry CH2Cl2 (191 mL) under argon at −15° C. were added diethylaminosulfur trifluoride (3.14 mL, 23.73 mmol, 1.5 eq) and, after 2 min, N-bromosuccinimide (3.66 g, 20.57 mmol, 1.3 eq). After being stirred at −15° C. for 30 min the reaction was diluted with CH2Cl2 (420 mL) and poured into a cold saturated aqueous NaHCO3 solution (195 mL). The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography on silica gel (petroleum ether/EtOAc 94:6) afforded 11 as viscous syrup (6.3 g, 73%).

후처리

  1. dry with materialThe organic layer was dried over MgSO4
  2. concentrationconcentrated
  3. customPurification by flash chromatography on silica gel (petroleum ether/EtOAc 94:6)

출처 및 근거

ORD 기록
ord-1c29419f07504d2ab5eb1c6bfcd3f456
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08211859B2

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