MDPSCL2: a new protecting group for chemoselective synthesis of 2'-O-alkylated guanosines.

Suetying Chow, Ke Wen, Yogesh S Sanghvi, Emmanuel A Theodorakis

Index: Nucleosides Nucleotides Nucleic Acids 22(5-8) , 583-7, (2003)

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Abstract

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.