473278-52-3Relevant academic research and scientific papers
Novel synthesis of 2′-O-methylguanosine
Chow, Suetying,Wen, Ke,Sanghvi, Yogesh S.,Theodorakis, Emmanuel A.
, p. 1631 - 1634 (2003)
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), (MDPSCl2, 2) as a new 3′,5′-O-protecting group for nucleosides. Use of CH3Cl 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.
MDPSCL2: a new protecting group for chemoselective synthesis of 2'-O-alkylated guanosines.
Chow, Suetying,Wen,Sanghvi, Yogesh S,Theodorakis, Emmanuel A
, p. 583 - 587 (2007/10/03)
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.
Reagent and process for protecting active groups
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Page column 34, (2008/06/13)
Silylating reagents having a group other than a divalent oxygen separating two silyl groups provide regioselective protection of reactive groups under robust conditions, such as basic conditions used in alkylation, acylation and deoxygenation. In particular, silylating reagents having a group other than oxygen separating two silyl groups are useful for protecting two hydroxy groups of a ribonucleic or deoxyribonucleic acid. Alkylation of a 2′-hydroxy group of a ribonucleoside protected with the inventive silylating agents in the presence of an excess of a mild hindered base such as sodium HMDS may be carried out without protecting the exocyclic amine and oxo functionalities of nucleobases.
Synthesis of 2'-O-methoxyethylguanosine using a novel silicon-based protecting group.
Wen,Chow, Suetying,Sanghvi, Yogesh S,Theodorakis, Emmanuel A
, p. 7887 - 7889 (2007/10/03)
A short and efficient synthesis of 2'-O-methoxyethylguanosine (8) is described. Central to this strategy is the development of a novel silicon-based protecting group (MDPSCl(2), 2) used to protect the 3',5'-hydroxyl groups of the ribose. Silylation of guanosine with 2 proceeded with excellent regioselectivity and in 79% yield. Alkylation of the 2'-hydroxyl group of 6 proceeded with methoxyethyl bromide and NaHMDS and afforded compound 7 in 85% yield, without any noticeable cleavage of the silyl protecting group and without the need to protect the guanine base moiety. Finally, deprotection of 7 was achieved using TBAF and produced 8 in 97% yield.
