MDPSCL2: a new protecting group for chemoselective synthesis of 2'-O-alkylated guanosines.
An improved strategy for the synthesis of 2'-O-methyl-guanosine (6) and 2'-MOE-guanosine (8) is reported. The regioselectivity of the alkylation was attained using a novel silicon-based protecting group, methylene-bis (diisopropyl-silylchloride) (MDPSCl2, 2). The alkylation proceeded in a chemoselective manner using NaHMDS as the base and MeCl or MOE-Br as the appropriate electrophiles.
Chow
Suetying
S
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, USA.
Wen
Ke
K
Sanghvi
Yogesh S
YS
Theodorakis
Emmanuel A
EA
D000478:Alkylation; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D017655:Silicon Compounds; D012833:Siloxanes
D007202:Indicators and Reagents; D017655:Silicon Compounds; D012833:Siloxanes; C479162:methylene-bis (diisopropyl-silylchloride); D006151:Guanosine; C031036:1,3-dichlorotetraisopropyldisiloxane