PRODUCTION OF ADENOSINE DERIVATIVE HAVING CARBON CHAIN SUBSTITUENT ON 2-POSITION

• Main Authors: HAYAKAWA HIROYUKI, TANAKA HIROMICHI, MIYASAKA SADA, KATO KEISUKE
• Format: Patent
• Language: English
• Published: 04.03.1997
• Edition: 6
• Subjects: CHEMISTRY; CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION ORPROCESSING OF GOODS; DERIVATIVES THEREOF; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS; SUGARS; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINSTCLIMATE CHANGE

PROBLEM TO BE SOLVED: To obtain the subject compound by lithiating a specific nucleoside containing a halogen in the base part, reacting with a tin compound to effect the stannylation of the compound, aminating the base part and introducing a carbon chain into the base part by Stille reaction. SOLUTION: The objective adenosine derivative having a carbon chain substituent on 2-position and expressed by formula III is produced by reacting a nucleoside expressed by formula I (R2 is H or a hydroxy-protective group; X is a halogen) with a lithiation agent (e.g. n-butyllithium) and a trialkyltin (e.g. tributyltin chloride) to effect the stannylation of the 2-position and obtain a compound expressed by formula II (R3 is a lower alkyl), adding ammonia water to a THF solution of the compound, heating for 42hr at 90 deg.C in a sealed tube to aminate the 6-position of the base part, introducing a carbon chain to the 2-position of the base part by Stille reaction comprising the reaction with tetrakistriphenyl phosphine palladium, cuprous iodide and iodobenzene, etc., and, as necessary, removing the hydroxyl-protecting group of the sugar part.