Thymidine → Thymidine, 5'-azido-5'-deoxy-

HRID 985633노트

반응식

HRID 985633 반응식
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6]O)[C@@H:3]([OH:4])[CH2:2]1.[N-:18]=[N+:19]=[N-:20].[Li+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>>[N:18]([CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])=[N+:19]=[N-:20]

참가 물질

5

반응물 4

HCID 5789ThymidineHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine2회HCID 88163Lithium azide

생성물 1

HCID 451456Thymidine, 5'-azido-5'-deoxy-

실험 절차

Thymidine (2.42 g, 10.0 mmol) was dried under reduced pressure for 1 hour. Thereto was added 2.20 g (4.5 eq) of lithium azide, and the mixture was further dried for 1 hour. Distilled DMF (50 ml) was added to the reaction vessel, and the pressure was reduced for about 10 minutes with stirring. Further, 3.41 g (1.3 eq) of triphenylphosphine was added and, after confirmation of the dissolution of triphenylphosphine, 4.97 g (1.5 eq) of carbon tetrabromide was added to initiate the reaction. On that occasion, the solution turned yellow. After 40 minutes, the completion of the reaction was confirmed by TLC, and the reaction was quenched with methanol. The solution was distilled under reduced pressure, and the residue was purified by silica gel column chromatography (mobile phase MeOH:CHCl3=1:9) to give 5′-azido-5′-deoxythymidine.

후처리

  1. customthe mixture was further dried for 1 hour
  2. additionDistilled DMF (50 ml) was added to the reaction vessel
  3. additionwas added
  4. customthe reaction
  5. waitAfter 40 minutes
  6. customthe reaction was quenched with methanol
  7. distillationThe solution was distilled under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (mobile phase MeOH:CHCl3=1:9)

출처 및 근거

ORD 기록
ord-ec3ed4f044a14a91a6275c0848e943a5
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872809B2

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