Dimethyl Sulfoxide → 2'-O-Nonylguanosine

HRID 1066409Notes

Reaction equation

HRID 1066409 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 0.1 M sodium phosphate buffer (50 ml, pH 7.4), 0.1 M 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-0495ad6420244856b07bd9154908fe92
Source dataset
uspto-grants-2001_06
Patent number
US06242592B1

Reaction notes

Loading…