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

HRID 6271

반응식

HRID 6271 반응식
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][C@@H:13]([O:16][CH2:17][P:18]([O:23]CC)([O:20]CC)=[O:19])[CH2:14][OH:15])=[C:4]([O:26]C)[N:3]=1.C[Si](Br)(C)C>CN(C)C=O>[OH:15][CH2:14][C@H:13]([O:16][CH2:17][P:18]([OH:20])([OH:23])=[O:19])[CH2:12][O:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:26])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 54289305(S)-2-amino-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-methoxypurine

생성물 1

HCID 135925074(S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]guanine수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-2-amino-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-methoxypurine (0.56 g, 1.38 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.82 ml, 13.8 mmol) and the solution stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue co-evaporated with acetone/water 1:1 (x2). The white solid obtained was crystallised from hot water to give the title compound as a white solid (0.305 g, 66%). IR:νmax (KBr) 3380, 3320, 3160, 1715, 1645, 1600, 1385, 1185, 1160, 1100, 1060, 1045, 925, 770 cm-1. 1H NMR: δH (D2O+NH3) 3.61 (1H, dd, J=12.1 Hz J=9.9 Hz, CHBP), 3.65-3.75 (2H, m, CHAP, CHBOH), 3.82-3.89 (1H, m, CH), 3.93 (1H, dd, J=12.3 Hz, J=3.6 Hz, CHAOH), 4.46-4.53 (2H, m, NOCH2), 8.03 (1H, s, H-8). Found: C, 32.24; H, 4.16; N, 20.59%. C9H14N5O7P requires: C, 32.24; H, 4.21; N, 20.89%. m/z: (FAB, thioglycerol matrix) 336 (MH+). [α]D25 (0.1M NaOH)+12.8° (c=0.43).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe white solid obtained
  3. customwas crystallised from hot water

출처 및 근거

ORD 기록
ord-45efcb5ccf7b442ba9f977b45016c6dc
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

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