Dimethyl Sulfoxide → 2'-O-Octadecylguanosine

HRID 368716Notes

Reaction equation

HRID 368716 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:35][C@H:34]([CH2:36][OH:37])[C@@H:32]([OH:33])[C@H:12]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:4](N)[N:3]=1.CS(C)=[O:41].[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:32]([OH:33])[C@@H:34]([CH2:36][OH:37])[O:35][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:41])[C:5]=2[N:6]=[CH:7]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 60961Adenosine2×HCID 117311872,6-Diamino-9-(2-O-octadecyl-beta-D-ribofuranosyl)purine

Product 1

HCID 1355097442'-O-Octadecylguanosine

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

2,6-Diamino-9-(2'-O-octadecyl-β-D-ribofuranosyl)purine (10 g) in 0.1 M sodium phosphate buffer (50 ml, pH 7.4), 0.1 M tris buffer (1000 ml, pH 7.4) and DMSO (1000 ml) was treated with adenosine deaminase (1.5 g) as per the procedure of Example 3. At day 3, day 5 and day 7 an additional aliquot (500 mg, 880 mg and 200 mg, respectively) of adenosine deaminase was added. The reaction was stirred for a total of 9 day and after purification by silica gel chromatography yielded the product (2 g). An analytical sample was recrystallized from MeOH 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH3), 1.22 [s, 32, O--CH2 --CH2 --(CH2)16 ], 5.07 (m, 2, 3'-OH5'-OH); 5.78 (d, 1, 1'-H); 6.43 (s, 2, NH2), 7.97 (s, 1, 8-H) and 10.64 (s, 1, NH2). Anal. Calcd. for C28H49N5O5 : C, 62.80; H, 9.16; N, 12.95. Found: C, 62.54; H, 9.18; N, 12.95.

Workup

  1. waitAt day 3, day 5 and day 7 an additional aliquot (500 mg, 880 mg and 200 mg
  2. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-0fc5e0e066444dd585f3420dcc91b46e
Source dataset
uspto-grants-2000_10
Patent number
US06133438

Reaction notes

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