Reaktion #351911

ord-ff2aefd7735844e3b8b6440118a88caa

Reaktionsgleichung

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3OCCCCn3ccnc3)c2n1
2,6-diamino-9-[2'-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine
Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](OCCCCn4ccnc4)[C@H]3O)c2n1
2,6-diamino-9-[3'-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine
→
Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCCCn2ccnc2)c(=O)[nH]1
2'-O-(Imidazol-1-yl)butylguanosine

Edukte

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
—
NaSO4
Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3OCCCCn3ccnc3)c2n1
2,6-diamino-9-[2'-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine
Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](OCCCCn4ccnc4)[C@H]3O)c2n1
2,6-diamino-9-[3'-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine

Reagenzien

Keine

Lösungsmittel

CS(C)=O
DMSO

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONThe product containing fractions
  2. 2
    Sonstigeare purified by silica gel chromatography
  3. 3
    workup.ADDITIONthe product containing fraction
  4. 4
    Sonstigeevaporated
  5. 5
    Sonstigeto give the product

Vorschrift

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 is treated with adenosine deaminase at RT for 5 days as per the procedure of Example 3. The product containing fractions are purified by silica gel chromatography and the product containing fraction evaporated to give the product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05646265uspto-grants-1997_07