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Oxygen → 1-[5-O-Benzoyl-2-deoxy-4-ethynyl-3-O-methanesulfonyl-beta-D-threo-pentofuranosyl]thymine

HRID 215731
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HRID 215731 반응식
[C:1]([O:9][CH2:10][C@@:11]1([C:26]#[CH:27])[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[OH:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[Si]([O:39][S:40]([C:43](F)(F)F)(=O)=[O:41])(C)(C)C.O=O>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:9][CH2:10][C@@:11]1([C:26]#[CH:27])[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[O:25][S:40]([CH3:43])(=[O:41])=[O:39])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 977OxygenHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 115887611-[5-O-Benzoyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl]thymine

생성물 1

HCID 866392191-[5-O-Benzoyl-2-deoxy-4-ethynyl-3-O-methanesulfonyl-beta-D-threo-pentofuranosyl]thymine수율 88%

시약·촉매·용매 1

HCID 167845
palladium(II) acetate
촉매

실험 절차

To a stirring mixture of 4 (3.58 g, 8.72 mmol) and Et3N (6.1 ml, 43.6 mmol) was added Me3SiOSO2CF3 (2.56 mL, 13.0 mmol) at 0° C. under positive pressure of dry Ar. The mixture was stirred for 30 min at the same temperature, and then partitioned between CH2Cl2 and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The residue was dissolved in DMSO (12 mL). To this solution was added Pd(OAc)2 (98 mg, 0.44 mmol), and the mixture was stirred for 36 h under positive pressure of O2. The mixture was partitioned between EtOAc and brine. The organic layer was dried (Na2SO4), evaporated, and chromatographed on a silica gel column (hexane/EtOAc=5/1) to give 5 (3.13 g, 88%) as a white solid.

후처리

  1. custompartitioned between CH2Cl2 and sat. aqueous NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in DMSO (12 mL)
  5. customThe mixture was partitioned between EtOAc and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated
  8. customchromatographed on a silica gel column (hexane/EtOAc=5/1)

출처 및 근거

ORD 기록
ord-0e9360100908407eb80e35bfbcc30902
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193165B2

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