Reaktion #351908

ord-334178f152d84f1cadc11fcf7c1fb73f

Reaktionsgleichung

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

Edukte

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
CCCCCCCCCCCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)nc(N)nc21
2,6-Diamino-9-(2'-O-octadecyl-β-D-ribofuranosyl)purine
CS(C)=O
DMSO
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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

2,6-Diamino-9-(2'-O-octadecyl-β-D-ribofuranosyl)purine (10 g) in 0.1M sodium phosphate buffer (50 ml, pH 7.4), 0.1M 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'-OH 5'-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.

Quelle

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