Reaktion #351903

ord-2067f9578b4c4e5a934f6bdbdba47bad

Reaktionsgleichung

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)nc(N)nc21
2,6-diamino-9-(2'-O-nonyl-β-D-ribofuranosyl)purine
CCCCCCCCCO[C@H]1[C@@H](O)[C@H](n2cnc3c(N)nc(N)nc32)O[C@@H]1CO
2,6-diamino-9-(3'-O-nonyl-β-D-ribofuranosyl)purine
CS(C)=O
DMSO
→
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(=O)[nH]c(N)nc21
product
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(=O)[nH]c(N)nc21
2'-O-Nonylguanosine

Edukte

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
CCCCCCCCCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)nc(N)nc21
2,6-diamino-9-(2'-O-nonyl-β-D-ribofuranosyl)purine
CCCCCCCCCO[C@H]1[C@@H](O)[C@H](n2cnc3c(N)nc(N)nc32)O[C@@H]1CO
2,6-diamino-9-(3'-O-nonyl-β-D-ribofuranosyl)purine
CS(C)=O
DMSO

Reagenzien

Keine

Lösungsmittel

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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

A mixture of 2,6-diamino-9-(2'-O-nonyl-β-D-ribofuranosyl)purine and 2,6-diamino-9-(3'-O-nonyl-β-D-ribofuranosyl)purine (≈80:20 mixture, 29 g) in 0.1M sodium phosphate buffer (50 ml, pH 7.4), 0.1M tris buffer (1800 ml, pH 7.4) and DMSO (1080 ml) was treated with adenosine deaminase (1.6 g) as per the procedure of Example 3 to yield 60 g of product as an oil. An analytical product was purified by silica gel chromatography and recrystallized from EtOAc. m.p. 258°-259° C. 1H NMR (DMSO-d6) δ 0.96 (t, 3, CH3, J=7 Hz); 1.17 [m, 12, O--CH2 --CH2 --(CH2)6 ]; 1.42 [m, 2, O--CH2CH2 (CH2)6 ]; 3.27-3.61 (m, 4, H-5', O--CH2 (CH2)7 ]; 3.95 (m, 1, H-4'), 4.10-4.13 (m, 2, H-2', H-3'); 5.13-6.06 (m, 2, 3'-OH 5'-OH); 5.80 (d, 1, H-1', J=6.4 Hz); 6.47 (s, 2, 2-NH2); 7.98 (s, 1, 8-H) and 10.64 (s, 1, N1 amide). Anal. Calcd. for C19H31N5O5 : C, 55.73; H, 7.63; N, 17.10. Found: C, 55.67; H, 7.66; N, 17.02.

Quelle

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