Art

J-GLOBAL ID：202002269744013606   Reference number：20A0539976

N-GLYCOSYLATION REACTION OF THIO-GLYCOSIDE USING HYPERVALENT IODINE(III) REAGENT

超原子価ヨウ素(III)試薬を用いたチオグリコシドのN-グリコシル化反応

Author (6)： MORIMOTO Koji (Ritsumeikan Univ., Shiga, JPN) ,  YANASE Kana (Ritsumeikan Univ., Shiga, JPN) ,  IKEDA Takumi (Ritsumeikan Univ., Shiga, JPN) ,  UCHIKAWA Chihiro (Ritsumeikan Univ., Shiga, JPN) ,  KITA Yasuyuki (Ritsumeikan Univ., Shiga, JPN) ,  KAJIMOTO Tetsuya (Ritsumeikan Univ., Shiga, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 101  Issue： 2  Page： 621-630  Publication year： Jan. 01, 2020 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *Glycosylation ,  *glycoside ,  *thiosugar ,  aromatic iodine compound ,  *nitrogen heterocyclic compound ,  1,3-dipolar cycloaddition ,  *polynuclear aromatic compound ,  Lewis acid catalyst ,  acid catalytic reaction ,  C-N bond ,  Oxidative Coupling ,  *N-glycosylation ,  *Thioglycosides ,  hypervalent iodine compound ,  *benzotriazoles ,  aliphatic chlorine compound ,  sulfonic acid ,  aliphatic fluorine compound
Semi thesaurus term： *benzotriazole derivative ,  Oxidative Coupling reaction

JST classification (5)： Triazoles  (CF07084O) ,  Addition reaction,elimination reaction  (CF02030M) ,  Catalytic reactions(homogeneous system)  (CB06090Q) ,  Preparation of catalysts  (CB06110P) ,  Aromatic monocyclic halogen compounds  (CF05030H)

Substance index (23)： 1-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl)-1H-benzotriazole ,  1-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl)-4-phenyl-1H-1,2,3-triazole ,  1-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-glucopyranosyl)-4-(4-bromophenyl)-1H-1,2,3-triazole ,  4-(4-Methylphenyl)-1-(2-O,3-O,4-O,6-O-tetraacetyl-β-D-glucopyranosyl)-1H-1,2,3-triazole ,  1-(Phenylthio)-1-deoxy-β-D-glucopyranose tetraacetate ,  1-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-galactopyranosyl)-1H-benzotriazole ,  1-(2-O,3-O,4-O,6-O-Tetraacetyl-β-D-galactopyranosyl)-4-phenyl-1H-1,2,3-triazole ,  1-(Phenylthio)-1-deoxy-β-D-galactopyranose tetraacetate ,  1,2-Dichloroethane ,  4-(4-Bromophenyl)-1H-1,2,3-triazole ,  4-Phenyl-1H-1,2,3-triazole ,  1,1,1,3,3,3-Hexafluoro-2-propanol ,  Koser reagent ,  Phenyldiacetoxyiodine(III) ,  PIFA ,  Trimethylsilyl trifluoromethanesulfonate ,  Methylene chloride ,  Trifluoroboron・diethyl ether ,  Trifluoromethanesulfonic acid ,  Benzotriazole ,  [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(1,2,3-triazol-1-yl)oxan-2-yl]methyl acetate ,  [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[4-(4-chlorophenyl)-1,2,3-triazol-1-yl]oxan-2-yl]methyl acetate ,  [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[4-(4-bromophenyl)-1,2,3-triazol-1-yl]oxan-2-yl]methyl acetate

Reference (17)：

• (a) M. E. Taylor and K. Drickamer, Introduction to Glycobiology, 2006; (b) N. W. Owens and F. Schweizer, in Comprehensive Biotechnology, Second Edition, 2011, vol. 1, pp. 122-138; (c) X. Yu, K. Baruah, C. N. Scanlan, and M. Crispin, in Antibody Fc: Linking Adaptive and Innate Immunity, Elsevier Inc., 2013, pp. 179-194; (d) T. B. Parsons, W. B. Struwe, J. Gault, K. Yamamoto, T. A. Taylor, R. Raj, K. Wals, S. Mohammed, C. V. Robinson, J. L. P. Benesch, and B. G. Davis, Angew. Chem. Int. Ed., 2016, 55, 2361; (e) S. V. Moradi, W. M. Hussein, P. Varamini, P. Simerska, and I. Toth, Chem. Sci., 2016, 7, 2492.
• A. Kobata, Proc. Japan Acad. Ser. B, 2013, 89, 97.
• T. Kajimoto and M. Node, Curr. Top. Med. Chem., 2009, 9, 13.
• (a) G. J. van der Heden van Noort, M. G. van der Horst, H. S. Overkleeft, G. A. van der Marel, and D. V. Filippov, J. Am. Chem. Soc., 2010, 132, 5236; (b) H. Tanaka, Y. Iwata, D. Takahashi, M. Adachi, and T. Takahashi, J. Am. Chem. Soc., 2005, 127, 1630; (c) K. Tanaka, T. Miyagawa, and K. Fukase, Synlett, 2009, 1571; (d) B. Wang, Y. Liu, R. Jiao, Y. Feng, Q. Li, C. Chen, L. Liu, G. He, and G. Chen, J. Am. Chem. Soc., 2016, 138, 3926; (e) Y. Kobayashi, Y. Nakatsuji, S. Li, S. Tsuzuki, and Y. Takemoto, Angew. Chem. Int. Ed., 2018, 57, 3646.
• (a) L. V. Lee, M. L. Mitchell, S. J. Huang, V. V. Fokin, K. B. Sharpless, and C. H. Wong, J. Am. Chem. Soc., 2003, 125, 9588; (b) P. van der Peet, C. T. Gannon, I. Walker, Z. Dinev, M. Angelin, S. Tam, J. E. Ralton, M. J. McConville, and S. J. Williams, ChemBioChem, 2006, 7, 1384; (c) N. J. Agard, J. M. Baskin, J. A. Prescher, A. Lo, and C. R. Bertozzi, ACS Chem. Biol., 2006, 1, 644; (d) N. J. Agard, J. A. Prescher, and C. R. Bertozzi, J. Am. Chem. Soc., 2004, 126, 15046.

Terms in the title (4)： 超原子価ヨウ素 ,  試薬 ,  チオグリコシド ,  N-グリコシル化