Introduction of a benzoyl group onto riboside in aqueous solution: One- step synthesis of 6-chloropurine 2',3'-di-O-benzoylriboside

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4355-4358

  Kozai, Shigetada ^a   Takamatsu, Satoshi ^a,b   Izawa, Kunisuke ^a,b   Maruyama, Tokumi ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b AJINOMOTO CO INC   (Japan)

Author keywords

Acylation; Nucleosides; Protecting groups; Regioselection

Indexed keywords

6 CHLOROPURINE 2',3' DI ORTHO BENZOYLRIBOSIDE; NUCLEOSIDE; UNCLASSIFIED DRUG;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 0033523037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00747-9     Document Type: Article

References (13)

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8. 6. High-performance liquid chromatography: Apparatus of high-performance liquid chromatography (HPLC) were CCPD pump (Toso Co.) and SPD-M10A photo diode array UV-VIS detector (Shimadzu Co.). The HPLC conditions were as follows: the columns, connection with Cosmosil Guard Column 5C18-MS (4.6X 10 mm, Nacalai Tesque INC.) and Cosmosil Packed Column 5C18-MS (4.6×150 mm, Nacalai Tesque INC.); eluent, 10 mM phosphoric acid-MeOH (2 : 3) for the mono- and di-O-benzoate mixture; flow rate, 1 ml /min; column temperature, 50°C. Standard solutions were prepared as follows: 3′-O-benzoate 11.73 mg was dissolved in DMSO (50 ml) and 2′,3′-di-O-benzoate (3.90 mg) was dissolved in DMSO (20 ml).
9. Maruyama, T.; Kozai, S.; Satoh, Y.; Takamatsu, S.; Izawa, K. Chem. Pharm.Bull, Submitted.
10. a) Brown, A. D.; Robins, R. K. J. Amer. Chem. Soc., 1965, 87, 1145.
11. b) Gin, J. B.; Dekker, C. A. Biochem., 1968, 7, 1413.
12. +-6-chloropurine), 154, 156 (6-chloropurine), λmax (MeOH)/nm 264.
13. 5CO), 6.45 (1H, d, J 4.9. 1′-H), 6.42 (1H, dd, J 5.5, 4.9, 2′-H), 6.25 (1H, dd, J 5.5, 5.2, 3′-H), 4.94 (1H, dd, J 12.4, 3.3, 5′a-H), 4.85-4.87 (1H, m, 4′-H), 4.70 (1H, dd, J 12.4, 4.1, 5′b-H).