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

HRID 2185095Notes

Reaction equation

HRID 2185095 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ed99fbec9124498c9be0e2456a26e9f5
Source dataset
uspto-grants-2002_06
Patent number
US06399754B1

Reaction notes

Loading…