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Triphenylphosphine → HCID 10258600、化合物

HRID 1708103
ノート
印刷プレビュー

反応式

HRID 1708103 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

HCID 10258600HCID 10258600、化合物収率 28%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2f62586b1c7e465bb51f0ab4948b939e
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05356886

反応ノート

読み込み中…

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