Reaktion #429102

ord-9e6ee242e87446af86fc4dd98c065afb

Reaktionsgleichung

CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)nc(N)nc21
2,6-Diamino-9- (2'-O-methyl-β-D-ribofuranosyl)purine
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
→
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(=O)[nH]c(N)nc21
product
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(=O)[nH]c(N)nc21
2'-O-Methylguanosine

Edukte

—
II
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)nc(N)nc21
2,6-Diamino-9- (2'-O-methyl-β-D-ribofuranosyl)purine
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine

Reagenzien

Keine

Lösungsmittel

O=P([O-])([O-])[O-].[Na+].[Na+].[Na+]
sodium phosphate
CS(C)=O
DMSO

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe resulting suspension was cooled
  2. 2
    Filtrationfiltered
  3. 3
    Filtrationthe resulting filter cake
  4. 4
    Waschenwashed with H2O
  5. 5
    Trocknendried to a white solid (4.0 g)
  6. 6
    SonstigeThe solid was recrystallized from hot H2O

Vorschrift

2,6-Diamino-9- (2'-O-methyl-β-D-ribofuranosyl)purine (9.5 g) in 0.1M sodium phosphate buffer (200 ml, pH 7.4) and DMSO (25 ml) was treated with adenosine deaminase (Type II Sigma) at RT for 4 days. The resulting suspension was cooled and filtered and the resulting filter cake washed with H2O and dried to a white solid (4.0 g). The solid was recrystallized from hot H2O to yield 2.9 g of product. m.p. 236°-238° C. 1H NMR (DMSO-d6) δ3.3 (s, 3, OCH3), 3.53 and 3.6 (ABX, 2, H-5'), 3.87 (m, 1, H-4'), 4.15 (m, 1, H-2'), 4.25 (m, 1, H-3'), 5.13 (t, 1, 5'-OH), 5.23 (d, 1, 3'-OH), 5.8 (d, 1, H-1'), 6.48 (br s, 2, NH2), 7.96 (s, 1, H-8) and 10.68 (br s, 1, NH). Anal. Calcd. for C11H15N5O5.1/2H2O: C, 43.14; H, 5.26; N, 22.86. Found: C, 43.59; H, 5.34; N, 23.04.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05856466uspto-grants-1999_01