title: Design and synthesis of regioselective cleaving reagents for oligonucleotides.
abstract: Reaction of methyl 2,3-anhydro-alpha-D-ribofuranoside with allylmagnesium chloride selectively took place at the 2-C position to afford methyl 2-C-allyl-2-deoxy-alpha-D-arabinofuranoside. 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose reacted with allylic alcohols in the presence of BF3.OEt2 to give the corresponding allyl beta-D-ribofuranosides. The allyl group in these compounds were converted into a variety of functional groups which include bromoacetoxy, oxylanyl, tosyloxy, and azide.
authors.affiliation: Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University, Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Mori
authors.forename: Y
authors.initials: Y
authors.lastname: Ohgo
authors.forename: H
authors.initials: H
authors.lastname: Tanaka
authors.forename: A
authors.initials: A
authors.lastname: Katoh
authors.forename: H
authors.initials: H
authors.lastname: Kaji
authors.forename: T
authors.initials: T
authors.lastname: Samejima
authors.forename: O
authors.initials: O
authors.lastname: Mitsunobu
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D007202:Indicators and Reagents; D009841:Oligonucleotides; C084403:methyl 2-C-allyl-2-deoxyarabinofuranoside; C084404:allyl ribofuranoside; D012266:Ribose; D001089:Arabinose