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Triphenylphosphine → HCID 10258600, 화합물

HRID 1708103
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HRID 1708103 반응식
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Si:11]([O:28][CH2:29][CH:30]([CH2:43]O)/[CH:31]=[CH:32]/[P:33](=[O:42])([O:38][CH:39]([CH3:41])[CH3:40])[O:34][CH:35]([CH3:37])[CH3:36])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O>[Si:11]([O:28][CH2:29][CH:30](/[CH:31]=[CH:32]/[P:33]([O:38][CH:39]([CH3:41])[CH3:40])([O:34][CH:35]([CH3:36])[CH3:37])=[O:42])[CH2:43][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[Cl:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53592776-ChloropurineHCID 10436173diisopropyl (E)-3-(t-butyldiphenylsilyloxy)methyl-4-hydroxybut-1-enylphosphonate

생성물 1

HCID 10258600HCID 10258600, 화합물수율 28%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 6-chloropurine (213 mg, 1.37 mmol), diisopropyl (E)-3-(t-butyldiphenylsilyloxy)methyl-4-hydroxybut-1-enylphosphonate (694 mg, 1.37 mmol) and triphenyl phosphine (540 mg, 2.06 mmol) in N,N-dimethylformamide (22 ml) stirred at 0° C. under dry nitrogen was added diethyl azodicarboxylate (358 mg, 2.06 mmol). The solution was stirred at room temperature for 16 h. The solvent was removed and the residue purified by column chromatography on silica gel eluting with acetone-hexane (1:4, 1:2) then ethyl acetate-methanol (99:1, 9:1) to give (E)-9-[2-(t-butyldiphenylsilyloxy) methyl-4-(diisopropoxyphosphoryl)but-3-enyl]-6-chloropurine as a colourless gum (244 mg, 28%); λmax (EtOH) 265 (9,215nm; υmax (film) 2980, 2930, 1590, 1560, 1425, 1385, 1335 and 1245 cm-1 ; δH (CDCl3) 1.10 (9H, s, CH3), 1.20 (12H, m, CH (CH3)2), 3.07 (1H, m, CH), 3.69 (2H, d, J 6 Hz, CH2O ), 4.50 (4H, m, CH2N and CH(CH3)2), 5.57 (1H, pseudo-t, J 17 Hz, PCH=CH), 6.66 (1H, ddd, J 8 Hz, 17 Hz and 26 Hz, PCH=CH), 7.30-7.70 (10H, m, Ph), 8.00 (1H, s, H-2/H-8), 8.73 (1H, s, H-2/H-8) (Found: M+ 641.2459. C32H42N4ClO4PSi requires M+ 641.2479).

후처리

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with acetone-hexane (1:4, 1:2)

출처 및 근거

ORD 기록
ord-2f62586b1c7e465bb51f0ab4948b939e
출처 데이터셋
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05356886

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