Reaktion #462337

Reaktionsgleichung

sodium methoxide

2-[(R)-2-amino-1-propylthio]benzothiazole hydrochloride

2-chloro-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine

2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-9H-purine

2',3',5'-tri-O-acetyl-2-amino-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine

→

2-amino-N-[(R)-1-(2-benzothiazolyl)thio2-propyl]adenosine

Ausbeute 19.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title compound was prepared

Vorschrift

The title compound was prepared according to general method A as described above in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]benzothiazole hydrochloride (prepared as described in Example 5) (7.13 g, 24 mmol) with 2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-9H-purine (Nucleic Acid Chemistry, Townsend L. B. and Tipson, R. S., eds., John Wiley and Sons Inc., 1986, 3, 144) (8.56 g, 20 mmol) followed by deacylation of a portion of the purified 2',3',5'-tri-O-acetyl-2-amino-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-amino-N-[(R)-1-(2-benzothiazolyl)thio2-propyl]adenosine (0.71 g, 19%) as a foam (following column chromatography) 1H NMR (DMSO-d6) δ 1.34 (3H, d, --CHCH3), 3.50-3.73 (4H, m, H-5'a and H-5'b and --CH2 --), 3.90 (1H, q, H- 4'), 4.10 (1H, d, H-3'), 4.51 (1H, q, H-2'), 5.11, 5.37 (2H, 2d, 2'- and 3'-OH), 5.40 (1H, t, 5'-OH), 5.73 (1H, d, H-1'), 5.79 (1H, br, --NH2), 7.36, 7.47 (2H, 2t, Ar-H), 7.92 (1H, s, H-8), 8.0 (1H, d, N--H). HPLC retention time 13.5 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].

Quelle