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

HRID 264722Notes

Reaction equation

HRID 264722 reaction equation
[CH2:1]([O:10][C@@H:11]1[C@H:15]([OH:16])[C@@H:14]([CH2:17][OH:18])[O:13][C@H:12]1[N:19]1[C:29]2[N:28]=[C:26]([NH2:27])[NH:25][C:23](=[O:24])[C:22]=2[N:21]=[CH:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C[Si](Cl)(C)C.[C:35](Cl)(=[O:39])[CH:36]([CH3:38])[CH3:37]>N1C=CC=CC=1>[C:35]([NH:27][C:26]1[NH:25][C:23](=[O:24])[C:22]2[N:21]=[CH:20][N:19]([C:29]=2[N:28]=1)[C@@H:12]1[O:13][C@H:14]([CH2:17][OH:18])[C@@H:15]([OH:16])[C@H:11]1[O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:39])[CH:36]([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 62325Isobutyryl chlorideHCID 1359803682'-O-Nonylguanosine

Product 1

HCID 136109000N2-Isobutyryl-2'-O-nonylguanosine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2'-O-nonylguanosine (14.7 g) in pyridine (360 ml) was treated with trimethylsilyl chloride (23.4 ml) and isobutyryl chloride (30.6 ml) as per the procedure of Example 4 to yield crude product (37 g). The crude material was purified by silica gel chromatography (eluted with 90/10 CHCl3 /MeOH) to yield 14.6 g of product re-crystallized from EtOAc. m.p. 168°-169° C. 1H NMR (DMSO-d6) δ 0.85 [t, 3, CH3 (nonyl)], 1.14 [m, 18, O--CH2CH2 (CH2)6, CH(CH3)2 ], 1.40 [m, 2, O--CH2CH2 (CH2)6 ], 2.79 [m, 1, CH(CH3)2 ], 3.31-3.63 (m, 4, H-5', O--CH2 (CH2)7 ]; 3.96 (m, H-4'), 4.27-4 37 (m, 2, H-2', H-3'); 5.10 (t, 1, 5'-OH, J=5 Hz), 5.18 (d, 1, 3'-OH, J=4 Hz), 5.91 (d, 1, H-1', J=6.6 Hz), 8.31 (s, 1, 8-H), 11.73 (s, 1, C2 amide) and 12.11 (s, 1, N1 amide). Anal. Calcd. for C23H37N5O6 : C, 57.60; H, 7.78; N, 14.60. Found: C, 57.63; H, 7.92; N, 14.62.

Workup

  1. customto yield crude product (37 g)
  2. customThe crude material was purified by silica gel chromatography (eluted with 90/10 CHCl3 /MeOH)

Sources & evidence

ORD record
ord-56815e5d89e54163ab999b4f2343f98e
Source dataset
uspto-grants-1997_07
Patent number
US05646265

Reaction notes

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