title: Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose.
abstract: We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel® resins. TentaGel® enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-101 Ookayama, Meguro, Tokyo 152-8552, Japan.
authors.forename: Ryota
authors.initials: R
authors.lastname: Takeuchi
authors.affiliation: Yokohama University of Pharmacy, 601, Matana-cho, Totsuka-ku, Yokohama, Kanagawa 245-0066, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Sakai
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-101 Ookayama, Meguro, Tokyo 152-8552, Japan. Electronic address: thiroshi@apc.titech.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
authors.affiliation: Yokohama University of Pharmacy, 601, Matana-cho, Totsuka-ku, Yokohama, Kanagawa 245-0066, Japan. Electronic address: ttak@ym.hamayaku.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
mesh_terms: D002384:Catalysis; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D054879:Halogenation; D008362:Mannosides / Q000737:chemistry*; D015394:Molecular Structure; D044367:Phase Transition; D011108:Polymers / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D013441:Sulfinic Acids / Q000737:chemistry
chemical_list: C000611187:2-fluoroglucose; D005960:Glucosides; D008362:Mannosides; D011108:Polymers; D013441:Sulfinic Acids; C048899:sulfuryl fluoride; D005947:Glucose
keywords: Fluorination; Glucose; Positron emission tomography; Solid-supported reagents; Sulfonate linker