title: Efficient large-scale synthesis of 5'-O-dimethoxytrityl-N4-benzoyl-5-methyl-2'-deoxycytidine.
abstract: An efficient process to synthesize 5'-O-dimethoxytrityl-N4-benzoyl-5-methyl-2'-deoxycytidine in high yield and quality is described. Final benzoylation was improved by developing a method to selectively hydrolyze benzoyl ester impurities. This inexpensive approach was scaled up to multikilogram quantities for routine use in oligonucleotide therapeutics.
authors.affiliation: Isis Pharmaceuticals, Inc., 2282 Faraday Ave., Carlsbad, CA 92008, USA.
authors.forename: Bruce S
authors.initials: BS
authors.lastname: Ross
authors.forename: Mingming
authors.initials: M
authors.lastname: Han
authors.forename: Vasulinga T
authors.initials: VT
authors.lastname: Ravikumar
mesh_terms: D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: C513442:5'-O-dimethoxytrityl-N(4)-benzoyl-5-methyl-2'-deoxycytidine; D003841:Deoxycytidine