Chow Suetying, Wen Ke, Sanghvi Yogesh S, Theodorakis Emmanuel A
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla 92093-0358, USA.
Bioorg Med Chem Lett. 2003 May 19;13(10):1631-4. doi: 10.1016/s0960-894x(03)00291-9.
An efficient and chemoselective synthesis of 2'-O-methylguanosine (6) has been accomplished in high yield without protection of the guanine base. The salient feature of the synthesis of 6 lies in the application of methylene-bis-(diisopropylsilyl chloride), (MDPSCl(2), 2) as a new 3',5'-O-protecting group for nucleosides. Use of CH(3)Cl as a weak electrophile and NaHMDS as a mild base was crucial to the success of the 2'-O-methylation of 3',5'-O-protected guanosine.
在不保护鸟嘌呤碱基的情况下，高效且化学选择性地合成了2'-O-甲基鸟苷（6），产率很高。6的合成的显著特点在于使用亚甲基双（二异丙基甲硅烷基氯）（MDPSCl₂，2）作为核苷新的3'，5'-O保护基团。使用CH₃Cl作为弱亲电试剂和NaHMDS作为温和碱对于3'，5'-O保护的鸟苷的2'-O-甲基化的成功至关重要。
