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Sodium Azide → 5'-azido-3'-O-t-butyldimethylsilyl-5'-deoxythymidine

HRID 1489361
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HRID 1489361 반응식
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14]I)[O:12][C@@H:11]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][N:25]=[N+:26]=[N-:27])[O:12][C@@H:11]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 103898023'-O-t-butyldimethylsilyl-5'-iodo-5'-deoxythymidine

생성물 1

HCID 148429675'-azido-3'-O-t-butyldimethylsilyl-5'-deoxythymidine수율 90%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a stirred solution of the 3'-O-t-butyldimethylsilyl-5'-iodo-5'-deoxythymidine (10.8 g, 20 mmol) prepared according to the method of Example 25 in dry DMF (50 ml) was added sodium azide (3.9 g, 60 mmol) and the mixture heated at 0° C. for 12 hours. Then the reaction mixture was diluted with ethyl acetate (200 ml) washed with water (2×50 ml) and brine (50 ml) and then dried with sodium sulfate. The title compound was purified by flash chromatography using 50% ethyl acetate in hexance in 90% yield.

후처리

  1. washwashed with water (2×50 ml) and brine (50 ml)
  2. dry with materialdried with sodium sulfate
  3. customThe title compound was purified by flash chromatography

출처 및 근거

ORD 기록
ord-930b811d07bf42cd8e5308065187aace
출처 데이터셋
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05677439

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