Ribosylation of the Base Residue of Inosine Derivatives by Phase-Transfer Catalysis |
| |
Authors: | Keiichi Aritomo Chihiro Urashima Takeshi Wada Mitsuo Sekine |
| |
Affiliation: | Department of Life Science , Tokyo Institute of Technology , Nagatsuta, Midoriku, Yokohama , 226 , Japan |
| |
Abstract: | Abstract Reaction of 2′,3′,5′-O-silylated inosine derivative 1 with 2, 3-O-isopropylidene-5-O-tritylribosyl chloride (3) in a two-phase (CH2Cl2-aq. NaOH) system in the presence of Bu4NBr gave three products, i. e., 6-O-α-, 6-O-β-, and N 1-β-isomers of glycosides 4, 5a, and 5b. A similar PTC reaction of 1 with 2, 3, 5-tri-O-benzylribosyl bromide (9) gave four regio- and stereo-isomers involving the N1-β-glycoside 10. Reaction of 1 with 2, 3, 5-tri-O-benzoylribosyl bromide (11) afforded three products involving the desired N1-β-glycoside 12b, which could be deprotected to give N 1-ribosylinosine (15b) as a useful intermediate for the synthesis of cIDPR. |
| |
Keywords: | |
|
|