Pyridine → Ortho-nitrobenzyl-2'-deoxyadenosine

HRID 611463노트

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HRID 611463 반응식
[N+:1]([C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][C@@:7]1([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1O)([O-:3])=[O:2].N1C=CC=CC=1.C(N(CC)CC)C>O>[N+:1]([C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][C@@:7]1([N:16]2[C:25]3[N:24]=[CH:23][N:22]=[C:20]([NH2:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:8]1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 8471TriethylamineHCID 70146783Ortho-nitrobenzyladenosine

생성물 1

HCID 66830961Ortho-nitrobenzyl-2'-deoxyadenosine수율 60.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 2'-deoxy-N -bis-ortho-nitrobenzyladenosine (200 mg, 0.518 mmol) was added anhydrous pyridine (10 ml) and evaporated to dryness. Pyridine (10 ml) was added followed by 4-4'-dimethoxytrityl chloride (900 mg, 2.3 mmol, 4.5 equiv.) and triethylamine (280 mg, 2.76 mmol, 4.0 equiv.) and stirred at room temperature under an argon atmosphere for 5 hours. Water (0.5 ml) was added and stirred for 20 minutes. The mixture was partitioned between ether and water (20 ml each) and the aqueous phase was re-extracted with ether (20 ml). The extracts were combined and washed with water (20 ml) and dried over anhydrous sodium sulfate, filtered and evaporated. The material was purified by chromatography on silica gel (4 g, using 0.7-2.5% methanol in methylene chloride) to yield 5'-O-DMT- N6 -bis-ortho-nitrobenzyl-2'-deoxyadenosine, (121 mg, 33%).

후처리

  1. customevaporated to dryness
  2. additionPyridine (10 ml) was added
  3. stirringstirred for 20 minutes
  4. customThe mixture was partitioned between ether and water (20 ml each)
  5. extractionthe aqueous phase was re-extracted with ether (20 ml)
  6. washwashed with water (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe material was purified by chromatography on silica gel (4 g, using 0.7-2.5% methanol in methylene chloride)

출처 및 근거

ORD 기록
ord-974859afdf2f44ef96650343e3f4d30a
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001611

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