2-Benzylthio-ATPalphaS
Chemical Name: 2-Benzylsulfanyl-5'-O-(1-thiotriphosphate)adenosine
CAS No. 246150-03-8 (R-isomer), 246150-04-9 (S-isomer), 246150-02-7 (undefined isomer)
项目整合开发状态: Biological Testing
项目研究机构: Bar-Ilan University (Originator), Universit?Montpellier I (Originator)
合成路线:Treatment of adenosine (I) with H2O2 and HOAc affords N-oxide (II),which is converted into the benzyloxime (IV) via N-benzyloxyadenosine perchlorate (III).Treatment of (IV) with CS2 and NaOH in MeOH followed by separation by filtration and chromatography yields 2-thioadenosine (V),which is then converted into the sodium thiolate salt by treatment with NaOH in MeOH and condensed with benzylbromide (VI) in DMF,providing derivative (VII).Finally,conversion of (VII) into the target compound is achieved by following these steps: (i) treatment of (VII) with thiophosphoryl chloride (PSCl3) in pyridine; (ii) addition of a mixture of Bu3N and (Bu3NH+)2P2O7H2 in DMF; and (iii) treatment with TEAB and chromatographic separation of regioisomers.
📌 参考资料/链接：
参考文献标题:2-Thiother 5'-O-(1-thiotriphosphate)adenosine derivatives as new insulin secretagogues acting through P2Y-receptors
文献作者:Fischer,B.; Chulkin,A.; Boyer,J.L.; Harden,K.T.; Gendron,F.P.; Beaudoin,A.R.; Chapal,J.; Hillaire-Buys,D.; Petit,P.
参考来源:J Med Chem 1999,42(18),3636
📄 详细内容
合成路线:Treatment of adenosine (I) with H2O2 and HOAc affords N-oxide (II),which is converted into the benzyloxime (IV) via N-benzyloxyadenosine perchlorate (III).Treatment of (IV) with CS2 and NaOH in MeOH followed by separation by filtration and chromatography yields 2-thioadenosine (V),which is then converted into the sodium thiolate salt by treatment with NaOH in MeOH and condensed with benzylbromide (VI) in DMF,providing derivative (VII).Finally,conversion of (VII) into the target compound is achieved by following these steps: (i) treatment of (VII) with thiophosphoryl chloride (PSCl3) in pyridine; (ii) addition of a mixture of Bu3N and (Bu3NH+)2P2O7H2 in DMF; and (iii) treatment with TEAB and chromatographic separation of regioisomers.
参考文献标题:Platelet aggregation inhibitors.IX.Chemical transformation of adenosine into 2-thioadenosine derivatives
文献作者:Kikugawa,K.; Suehiro,H.; Yanase,R.; Aoki,A.
参考来源:Chem Pharm Bull 1977,25(8),1959