title: Odorless benzenethiols in synthesis of thioglycosides and its application for glycosylation reactions.
abstract: p-Octyloxybenzenethiol (2) was synthesized as a new odorless benzenethiol. Moreover, preparation of thioglycosides using 2 and their application for glycosylation reactions were attempted. As a result, it was found that the thioglycosides were as excellent glycosyl donors as 4-dodecylphenyl 1-thio-glycosides, which were previously reported by our group, and more useful than the previous donors in terms of fine chemistry in glycosylation reaction activated with silver triflate and N-iodosuccinimide (NIS). In addition, this method was applicable to the sialylation with NIS and triflic acid. All procedures from the preparation of thioglycosides to the glycosylation reaction could be attained completely under conditions where no malodor was generated.
authors.affiliation: Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE program, Kyoto Pharmaceutical University, Misasagi, Kyoto 607-8412, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Kajimoto
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Ishioka
authors.forename: Takahiro
authors.initials: T
authors.lastname: Katoh
authors.forename: Manabu
authors.initials: M
authors.lastname: Node
mesh_terms: D000969:Antinematodal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002240:Carbohydrate Sequence; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000494:pharmacology; D013388:Succinimides / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: C515785:4-octyloxybenzenethiol; D000969:Antinematodal Agents; D008698:Mesylates; D010636:Phenols; D010647:Phenyl Ethers; D013388:Succinimides; D013438:Sulfhydryl Compounds; D013865:Thioglycosides; C008155:N-iodosuccinimide; C042983:thiophenol; D019158:N-Acetylneuraminic Acid; C012077:trifluoromethanesulfonic acid