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

HRID 2274449
ノート
印刷プレビュー

反応式

HRID 2274449 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 167845
palladium(II) acetate
触媒

実験手順

To a stirring mixture of 4 (3.58 g, 8.72 mmol) and Et3N (6.1 ml, 43.6 mmol) was added Me3SiOSO2 CF3 (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.

後処理

  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)

出典と根拠

ORDレコード
ord-c8e8134f88314af5aad4fc7e927cda68
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09126971B2

反応ノート

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