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

HRID 722759노트

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HRID 722759 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 136076155N2-Isobutyryl-2'-O-octadecylguanosine수율 55.9%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3d1422a9aa254a179bbda812f03659dc
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138517B2

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