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Revisiting Glycosylations Using Glycosyl Fluoride by BF3·Et2O: Activation of Disarmed Glycosyl Fluorides with High Catalytic Turnover.
Manabe, Yoshiyuki; Matsumoto, Takuya; Ikinaga, Yuka; Tsutsui, Yuya; Sasaya, Shota; Kadonaga, Yuichiro; Konishi, Akihito; Yasuda, Makoto; Uto, Tomoya; Dai, Changhao; Yano, Kumpei; Shimoyama, Atsushi; Matsuda, Ayana; Fukase, Koichi.
Afiliação
  • Manabe Y; Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Matsumoto T; Core for Medicine and Science Collaborative Research and Education Project Research Center for Fundamental Sciences Graduate School of Science Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Ikinaga Y; Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Tsutsui Y; Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Sasaya S; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Kadonaga Y; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Konishi A; Core for Medicine and Science Collaborative Research and Education Project Research Center for Fundamental Sciences Graduate School of Science Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Yasuda M; Division of Science, Institute for Radiation Sciences, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
  • Uto T; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Dai C; Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Yano K; Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Shimoyama A; Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Matsuda A; Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
  • Fukase K; Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
Org Lett ; 24(1): 6-10, 2022 01 14.
Article em En | MEDLINE | ID: mdl-34932362
Catalytic glycosylations with glycosyl fluorides using BF3·Et2O are presented. Glycosylations with both armed and disarmed donors were efficiently catalyzed by 1 mol% of BF3·Et2O in a nitrogen-filled glovebox without the use of dehydrating agents. Our finding is in sharp contrast with conventional BF3·Et2O-mediated glycosylations, where excess Lewis acid and additives are required. Mechanistic studies indicated that the chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Japão
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Japão