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Bromotrimethylsilane → (S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenine

HRID 6274
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인쇄 미리보기

반응식

HRID 6274 반응식
C([O:3][P:4]([CH2:9][O:10][C@@H:11]([CH2:24][OH:25])[CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6]CC)=[O:5])C.C[Si](Br)(C)C>ClCCl>[OH:25][CH2:24][C@H:11]([O:10][CH2:9][P:4]([OH:5])([OH:6])=[O:3])[CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 54312422(S)-9-[2-(diethoxyphosphorylmethoxy)3-hydroxypropoxy]adenine

생성물 1

HCID 54431837(S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]adenine수율 78.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]adenine (0.09 g, 0.24 mmol) in dry dichloromethane (3 ml) was added trimethylsilyl bromide (0.31 ml, 2.4 mmol) and the solution stirred at ambient temperature for 4 hours. The solvent was removed under reduced pressure and the residue co-evaporated with acetone/water 1:1 (x3). Crystallisation of the residue from water/acetone gave the title compound as a white solid (0.06 g, 78%), mp. 93°-198° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customCrystallisation of the residue from water/acetone

출처 및 근거

ORD 기록
ord-1700e5b3912a4121a6882d243c1ca8a2
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05247085

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