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Diethyl Ether → N3-Benzyloxymethyl-5'-O-tert-butyldiphenylsilylthymidine

HRID 429951
ノート
印刷プレビュー

反応式

HRID 429951 の反応式
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[OH:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[CH2:45][O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCOCC>C(Cl)Cl>[CH2:47]([O:46][CH2:45][N:28]1[C:29](=[O:30])[C:31]([CH3:32])=[CH:33][N:25]([C@@H:23]2[O:24][C@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C@@H:21]([OH:34])[CH2:22]2)[C:26]1=[O:27])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=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 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 118128465'-O-tert-Butyldiphenylsilyl-thymidine

生成物 1

HCID 10483731N3-Benzyloxymethyl-5'-O-tert-butyldiphenylsilylthymidine収率 88%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a stirred solution of 2 (117.0 g, 243.8 mmol) and Hunig's base (diisopropylethylamine, 63.0 g, 487.5 mmol) in CH2Cl2 (400 mL) at 23° C. was added a solution of benzyl chloromethyl ether (40.7 g, 260.0 mmol) over a 15 min. period. The resultant mixture was maintained at 23° C. and stirred for 14 h. Ether (1 L) was added to the mixture and the ethereal solution was washed with 10% aqueous HCl (1×100 mL) and H2O (200 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/AcOEt 40:1 then 10:1) to yield 128.9 g (88%) of 3 as a white solid. Rf(CH2Cl2/AcOEt 10:1) 0.31. 1H-NMR (CDCl3): 1.10 (s, 9H, C-Me3), 1.65 (s, 3H, 5-Me), 2.16 (m, 1H, 2′-Hβ), 2.41 (m, 1H, 2′-Hβ), 2.53 (br s, 1H 3′-OH), 3.84 (d, 1H, J=8.8 Hz, 5′-CHH), 3.98 (d, 1H, J=8.8 Hz, 5′-CHH), 4.01 (s, 1H, 4′-H), 6.64 (br s, 1H, 3′-H), 4.70 (s, 2H, OCH2Ph), 5.50 (s, 2H, NCH2O), 6.41 (dd, 1H, J=8.0, 5.8 Hz, 1′-H), 7.20-7.50 (m, 13H, aromatic-H), 7.65-7.69 (m, 3H, 6-H and aromatic-H). 13C-NMR (CDCl3): 12.86 (−5-CH3), 19.45 (+, C-Me3), 27.09 (−, C-Me3), 41.16 (+, 2′-C), 64.25 (+, 5′-C), 70.70 (+, O—C—Ph), 71.97 (−, 4′-C), 72.29 (+, N—C—C), 85.51 (−, 3′-C), 87.20 (−, 1′-C), 110.47 (+, 5-C), 127.72, 128.08, 128.36 (−, aromatic-C), 130.25 (−, 6-C), 132.42, 133.00 (+, aromatic-C) 134.39, 135.37, 135.62 (−, aromatic-C), 137.95 (+, aromatic-C), 151.01 (+, 2-C), 163.68 (+, 4-C).

後処理

  1. washthe ethereal solution was washed with 10% aqueous HCl (1×100 mL) and H2O (200 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/AcOEt 40:1

出典と根拠

ORDレコード
ord-c56e464a27fc4ec194eae5e57bda96fa
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06320040B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート