Chlorotrimethylsilane → N2-Isobutyryl-2'-O-octadecylguanosine

HRID 722759ノート

反応式

HRID 722759 の反応式
[CH2:1]([O:19][C@@H:20]1[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:21]1[N:28]1[C:38]2[N:37]=[C:35]([NH2:36])[NH:34][C:32](=[O:33])[C:31]=2[N:30]=[CH:29]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[Si](Cl)(C)C.[C:44](Cl)(=[O:48])[CH:45]([CH3:47])[CH3:46].[OH-].[NH4+]>N1C=CC=CC=1.O>[C:44]([NH:36][C:35]1[NH:34][C:32](=[O:33])[C:31]2[N:30]=[CH:29][N:28]([C:38]=2[N:37]=1)[C@@H:21]1[O:22][C@H:23]([CH2:26][OH:27])[C@@H:24]([OH:25])[C@H:20]1[O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:48])[CH:45]([CH3:47])[CH3:46]

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 14923Ammonium HydroxideHCID 62325Isobutyryl chlorideHCID 1355097442'-O-Octadecylguanosine

生成物 1

HCID 136076155N2-Isobutyryl-2'-O-octadecylguanosine収率 55.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

2′-O-Octadecylguanosine (1.9 g) in pyridine (150 ml) was cooled in an ice bath, and treated with trimethylsilyl chloride (2 g, 5 eq) and isobutyryl chloride (2 g, 5 eq). The reaction mixture was stirred for 4 hours, during which time it was allowed to warm to room temperature. The solution was cooled, water added (10 mL) and stirred for an additional 30 minutes. Concentrated ammonium hydroxide (10 mL) was added and the solution concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc) to yield 1.2 g of product. 1H NMR (DMSO-d6) δ 0.85 (t, 3, CH3), 1.15 (m, 38, O—CH2CH2(CH2)16 and CH(CH3)2), 2.77 (m, 1, CH(CH3)2), 4.25 (m, 2, 2′H, 3′H), 5.08 (t, 1, 5′-OH), 5.12 (d, 1, 3′-OH), 5.87 (d, 1, 1′-H), 8.27 (s, 1, 8-H), 11.68 (s, 1, NH2) and 12.08 (s, 1, NH2). Anal. Calcd. for C32H55N5O6: C, 63.47; H, 9.09; N, 11.57. Found: C, 63.53; H, 9.20; N, 11.52.

後処理

  1. temperatureThe solution was cooled
  2. stirringstirred for an additional 30 minutes
  3. concentrationthe solution concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-3d1422a9aa254a179bbda812f03659dc
出典データセット
uspto-grants-2006_11
特許番号
US07138517B2

反応ノート

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