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

HRID 368717Notes

Reaction equation

HRID 368717 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]>N1C=CC=CC=1>[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

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 62325Isobutyryl chlorideHCID 1355097442'-O-Octadecylguanosine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2'-O-octadecylguanosine (1.9 g) in pyridine (150 ml) was treated with trimethylsilyl chloride (2 g, 5 eq) and isobutyryl chloride (2 g, 5 eq) as per the procedure of Example 4. The product 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, 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. customThe product was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc)

Sources & evidence

ORD record
ord-0962a34806934902a5467b6d9faa84f2
Source dataset
uspto-grants-2000_10
Patent number
US06133438

Reaction notes

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