Odorless benzenethiols in synthesis of thioglycosides and its application for glycosylation reactions.
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.
Kajimoto
Tetsuya
T
Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE program, Kyoto Pharmaceutical University, Misasagi, Kyoto 607-8412, Japan.
Ishioka
Yuichi
Y
Katoh
Takahiro
T
Node
Manabu
M
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
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