Dimethyl Sulfoxide → 2'-O-Nonylguanosine

HRID 1720547Notes

Reaction equation

HRID 1720547 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:12]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:4](N)[N:3]=1.NC1N=C2C(N=CN2[C@@H]2O[C@H](CO)[C@@H](OCCCCCCCCC)[C@H]2[OH:42])=C(N)N=1.CS(C)=O.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH2:14]([O:13][C@@H:12]1[C@H:23]([OH:24])[C@@H:25]([CH2:27][OH:28])[O:26][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:42])[C:5]=2[N:6]=[CH:7]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 60961AdenosineHCID 15858694(2R,3R,4R,5R)-5-(2,6-Diamino-9H-purin-9-yl)-2-(hydroxymethyl)-4-(nonyloxy)tetrahydrofuran-3-olHCID 228747392,6-diamino-9-(3-O-nonyl-beta-D-ribofuranosyl)purine

Product 1

HCID 1359803682'-O-Nonylguanosine

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

A mixture of 2,6-diamino-9-(2-O-nonyl-β-D-ribofuranosyl)purine and 2,6-diamino-9-(3-O-nonyl-β-D-ribofuranosyl)purine (≈80:20 mixture, 29 g) in 0.1M sodium phosphate buffer (50 ml, pH 7.4), 0.1M tris buffer (1800 ml, pH 7.4) and DMSO (1080 ml) was treated with adenosine deaminase (1.6 g) as per the procedure of Example 3 to yield 60 g of product as an oil. An analytical product was purified by silica gel chromatography and recrystallized from EtOAc. m.p. 258°-259° C. 1H NMR (DMSO-d6) δ 0.96 (t, 3, CH3, J=7 Hz); 1.17 [m, 12, O--CH2 --CH2 --(CH2)6 ]; 1.42 [m, 2, O--CH2CH2 (CH2)6 ]; 3.27-3.61 (m, 4, H-5', O--CH2 (CH2)7 ]; 3.95 (m, 1, H-4'), 4.10-4.13 (m, 2, H-2', H-3'); 5.13-6.06 (m, 2, 3'-OH, 5'-OH); 5.80 (d, 1, H-1', J=6.4 Hz); 6.47 (s, 2, 2-NH2); 7.98 (s, 1, 8-H) and 10.64 (s, 1, N1 amide). Anal. Calcd. for C19H31N5O5 : C, 55.73; H, 7.63; N, 17.10. Found: C, 55.67; H, 7.66; N, 17.02.

Sources & evidence

ORD record
ord-f7692363117d47feabfad1826b9eb0fc
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

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