Acetic Anhydride → 1-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymine

HRID 1181912노트

반응식

HRID 1181912 반응식
[I:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@H:4]1[OH:17].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:17][C@H:4]1[C@@H:3]([CH2:2][I:1])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)(=[O:20])[CH3:19]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 128500761-(2,5-dideoxy-5-iodo-beta-D-threo-pentofuranosyl)thymine

생성물 1

HCID 121116121-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymine수율 77%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of 1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (for preparation see ref. J. Org. Chem. 1964, 29, 2076) (5.1 g, 14.5 mmol) in anhydrous pyridine (50 mL) at 0° C. under argon was added acetic anhydride (7.0 ml, 75.4 mmol). The reaction mixture was stirred at room temperature for 17 h. The reaction mixture was cooled with ice bath and quenched by slow addition of water (15 mL). The reaction mixture was stirred for 30 min and concentrated to dryness, and co-evaporated with anhydrous toluene three times. The residue was re-dissolved in dichloromethane and chromatographed on silica gel with 1-3% methanol in ethyl acetate gave 4.4 g of 1-(3-O-acetyl-2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (49).

후처리

  1. temperatureThe reaction mixture was cooled with ice bath
  2. customquenched by slow addition of water (15 mL)
  3. stirringThe reaction mixture was stirred for 30 min
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue was re-dissolved in dichloromethane
  6. customchromatographed on silica gel with 1-3% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-ab701c16beda478e803e1f513f351e98
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285658B2

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