Novel synthesis of 2'-O-methylguanosine.
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.
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla 92093-0358, USA.
Suetying
S
Chow
Ke
K
Wen
Yogesh S
YS
Sanghvi
Emmanuel A
EA
Theodorakis
D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008722:Methods; D008737:Methyl Chloride / Q000737:chemistry; D015394:Molecular Structure; D017655:Silicon Compounds / Q000737:chemistry
D017655:Silicon Compounds; C479162:methylene-bis (diisopropyl-silylchloride); D006151:Guanosine; D008737:Methyl Chloride; C024900:2'-O-methylguanosine