Adenosine → 2'-O-(Imidazol-1-yl)butylguanosine

HRID 1720555Notes

Reaction equation

HRID 1720555 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][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[C:4](N)[N:3]=1.NC1N=C2C(N=CN2[C@@H]2O[C@H](CO)[C@@H](OCCCCN3C=CN=C3)[C@H]2[OH:42])=C(N)N=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>CS(C)=O>[N:18]1([CH2:17][CH2:16][CH2:15][CH2:14][O:13][C@@H:12]2[C@H:23]([OH:24])[C@@H:25]([CH2:27][OH:28])[O:26][C@H:11]2[N:8]2[C:9]3[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:42])[C:5]=3[N:6]=[CH:7]2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 3

HCID 60961AdenosineHCID 228747352,6-Diamino-9-[2-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purineHCID 228747382,6-diamino-9-[3-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purine

Product 1

HCID 1360797852'-O-(Imidazol-1-yl)butylguanosine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the 2,6-diamino-9-[2-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine and 2,6-diamino-9-[3-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine isomers in 0.1M tris buffer (pH 7.4), 0.1M NaSO4 buffer (pH 7.4) and DMSO will treated with adenosine deaminase at RT for 5 days as per the procedure of Example 3. The product containing fractions will be purified by silica gel chromatography and the product containing fraction evaporated to give the product.

Workup

  1. additionThe product containing fractions
  2. customwill be purified by silica gel chromatography
  3. additionthe product containing fraction
  4. customevaporated
  5. customto give the product

Sources & evidence

ORD record
ord-c4923df7744649418bbb8847f0653d09
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

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