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J-GLOBAL ID：200902215324716260   Reference number：09A0817927

Remarkable Selectivity in Derivatization and Protection of Hydroxy Groups of 51-hydroxyCTX3C: Chemoselective Synthesis of Biotin-conjugated Ciguatoxin Derivatives

51ヒドロキシCTX3Cのヒドロキシル基の誘導体化及び保護の顕著な選択性 ビオチン共役シガトキシン誘導体の化学的選択性合成

Author (5)： ISHIHARA Yuuki (Dep. of Chemistry, Graduate School of Sci., Tohoku Univ.) ,  MIYAZAKI Keisuke (Dep. of Chemistry, Graduate School of Sci., Tohoku Univ.) ,  YAMASHITA Shuji (Dep. of Chemistry, Graduate School of Sci., Tohoku Univ.) ,  HIRAMA Masahiro (Dep. of Chemistry, Graduate School of Sci., Tohoku Univ.) ,  HIRAMA Masahiro (Res. and Analytical Centar for Giant Molecules, Graduate School of Sci., Tohoku Univ.)
Material： Chemistry Letters  (Chem Lett)
Volume： 38  Issue： 9  Page： 886-887 (J-STAGE)  Publication year： 2009 
JST Material Number： S0742A  ISSN： 0366-7022  CODEN： CMLTAG  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,...

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JST classification (3)： Oxygen heterocycles in general  (CF07020K) ,  Poisoning of animals  (FE02050I) ,  Toxicity of animal derived substances  (GZ03020U)

Substance index (7)： (2Z,5S,6R,7R,8S,9R,11S,12R,13Z,15S,16R,18Z,20S,21R)-20,22-Bis(tert-butyldimethylsiloxy)-1,6:5,9:8,12:11,16:15,21-pentaepoxy-2,13,18-docosatriene-7-ol ,  2-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-yl]pentanoyl]amino]acetic acid (2Z,5S,6S,7R,8R,9R,11S,12R,13Z,15S,16R,18Z,20S,21R,23Z,26S,27R,29R,30S,31R,33S,34R,36R,38S,39R,41S,42R,43S,44S,45S,46R,47S,48S,49S,51S)-29,44,51-trihydroxy-30,36,43,47,48-pentamethyl-1,6:5,9:8,12:11,16:15,21:20,27:26,31:30,34:33,39:38,42:41,46:45,49:49,52-tridecaepoxydopentacontane-2,13,18,23-tetraene-7-yl ester ,  2-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-yl]pentanoyl]amino]acetic acid (2Z,5S,6S,7R,8R,9R,11S,12R,13Z,15S,16R,18Z,20S,21R,23Z,26S,27R,29R,30S,31R,33S,34R,36R,38S,39R,41S,42R,43S,44S,45S,46R,47S,48S,49S,51S)-7,29,44-trihydroxy-30,36,43,47,48-pentamethyl-1,6:5,9:8,12:11,16:15,21:20,27:26,31:30,34:33,39:38,42:41,46:45,49:49,52-tridecaepoxydopentacontane-2,13,18,23-tetraene-51-yl ester ,  33-[[2-[2-[2-[2-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-yl]pentanoyl]amino]ethoxy]ethoxy]ethoxy]ethyl]amino]-5,33-dioxo-9,12,15,18,21,24,27,30-octaoxa-6-azatritriacontaneoic acid ,  3-[(1S,4S,5R,7S,8R,10R,12S,13R,15S,16R,17S,18S,19S,20R,21S,22S,23R,25S)-18,25-Dihydroxy-10,17,21,22-tetramethyl-1,5:4,8:7,13:12,16:15,20:19,23:23,26-heptaepoxy-2-oxahexacosane-1-yl]propanoic acid methyl ester ,  51-Hydroxy-CTX 3C ,  Biotin

Reference (29)：

• 1) L. C. Strachan, R. J. Lewis, G. M. Nicholson, J. Pharmacol. Exp. Ther. 1999, 288, 379.
• 2) a) P. J. Scheuer, Tetrahedron 1994, 50, 3.
•  b) R. J. Lewis, Toxicon 2001, 39, 97.
•  c) T. Yasumoto, M. Murata, Chem. Rev. 1993, 93, 1897.
•  d) T. Yasumoto, Chem. Rec. 2001, 1, 228.

Terms in the title (9)： CTX3C ,  ヒドロキシル基 ,  誘導体化 ,  選択性 ,  ビオチン ,  共役 ,  シガトキシン ,  誘導体 ,  化学