BIOMAT Database Logo BIOMAT Database Logo

Efficient large-scale synthesis of 5'-O-dimethoxytrityl-N4-benzoyl-5-methyl-2'-deoxycytidine. 2006

Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Isis Pharmaceuticals, Inc., 2282 Faraday Ave., Carlsbad, CA 92008, USA.

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.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003841 Deoxycytidine A nucleoside component of DNA composed of CYTOSINE and DEOXYRIBOSE. Cytosine Deoxyribonucleoside,Cytosine Deoxyriboside,Deoxyribonucleoside, Cytosine,Deoxyriboside, Cytosine
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Structure and conformation of 5-methoxymethyl-N4-methyl-2'-deoxycytidine.
November 1990, Acta crystallographica. Section C, Crystal structure communications,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Selective biocatalytic acylation studies on 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine: an efficient synthesis of UNA monomer.
January 2012, Nucleosides, nucleotides & nucleic acids,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
The synthesis of methyl 5-O-benzoyl-2,3-dideoxy-beta-D-glycero-pentofuranoside. IV. (Methyl 5-O-benzoyl-2,3-dideoxy-beta-D-ribofuranoside).
May 1967, Tetrahedron letters,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
N4-acyl-2'-deoxycytidine-5'-triphosphates for the enzymatic synthesis of modified DNA.
July 2018, Nucleic acids research,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Nucleosides. 33. N4-acylated 5-fluorocytosines and a direct synthesis of 5-fluoro-2'-deoxycytidine.
July 1966, Journal of medicinal chemistry,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Structure of 5-methyl-2'-deoxycytidine.
May 1988, Acta crystallographica. Section C, Crystal structure communications,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Preparation and properties of N4-alkyl analogues of 5-methyl-2'-deoxycytidine, their 5'-mono- and triphosphates, and N4-alkyl derivatives of 1,5-dimethylcytosine.
January 1969, Acta biochimica Polonica,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Large-scale synthesis of 5'-O-pixyl protected 2'-deoxynucleosides useful for oligonucleotide synthesis.
January 2005, Nucleosides, nucleotides & nucleic acids,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Elimination of band compression in sequencing gels by the use of N4-methyl-2'-deoxycytidine 5'-triphosphate.
June 1993, Nucleic acids research,
Bruce S Ross, and Mingming Han, and Vasulinga T Ravikumar
Concise and efficient synthesis of 3'-O-tetraphosphates of 2'-deoxyadenosine and 2'-deoxycytidine.
January 2015, Nucleosides, nucleotides & nucleic acids,
Copied contents to your clipboard!