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J-GLOBAL ID：200902235702512785   Reference number：09A0182498

STEREOSELECTIVE β-D-PSICOFURANOSYLATION AND SYNTHESIS OF β-D-PSICOFURANOSYLCERAMIDE

立体選択的β-D-プシコフラノシル化とβ-D-プシコフラノシルセラミドの合成

Author (2)： UENISHI Jun'ichi (Kyoto Pharmaceutical Univ., Kyoto, JPN) ,  UEDA Atsushi (Kyoto Pharmaceutical Univ., Kyoto, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 77  Issue： 2  Page： 1297-1305  Publication year： Feb. 01, 2009 
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： *glycosidation ,  glycoside ,  functional group protection ,  deprotection ,  asymmetric synthesis ,  *glycoside(except carbohydrate) ,  monosaccharide ,  sterol ,  alicyclic alcohol ,  aliphatic alcohol

JST classification (1)： Glycosides  (CF10057O)

Substance index (12)： 1-O-Benzyl-2-O,3-O-isopropylidene-L-threitol ,  1-O,6-O-Dibenzoyl-2-O-(4-methoxyphenyl)-3-O,4-O-isopropylidene-β-D-psicofuranose ,  1-O,6-O-Dibenzoyl-2-O-[(2S,3S)-2,3-[isopropylidenebis(oxy)]-4-(benzyloxy)butyl]-3-O,4-O-isopropylidene-β-D-psicofuranose ,  1-O,6-O-Dibenzoyl-2-O-isopropyl-3-O,4-O-isopropylidene-β-D-psicofuranose ,  4-Methoxyphenol ,  N-Boc-L-Serine methyl ester ,  Boc-O-(1-O,6-O-Dibenzoyl-3-O,4-O-isopropylidene-β-D-psicofuranosyl)-L-Ser-OMe ,  N-[(1S,2R,3E)-1-[(β-D-Psicofuranosyloxy)methyl]-2-hydroxy-3-heptadecenyl]octadecaneamide ,  Cholestanol ,  2-Propanol ,  Cholestane-3β-yl 1-O,6-O-dibenzoyl-3-O,4-O-isopropylidene-β-D-psicofuranoside ,  Phthalic acid 1-benzyl 2-(1-O,6-O-dibenzoyl-3-O,4-O-isopropylidene-β-D-psicofuranosyl) ester

Reference (11)：

• E. Bapreto-Bergter, M. R. Pinto, and M. L. Rodrigues, An. Acad. Bras. Cienc., 2004, 76, 67; R. X. Tan and J. H. Chen, Nat. Prod. Rep., 2003, 20, 509.
• E. Bieberich, Neurosignals, 2008, 16, 124; S. Pandey, R. F. Murphy, and D. K. Agrawal, Exp. Mol. Pathol., 2007, 82, 298; E. Guibins and P. L. Li, Am. J. Physiol. Regul. lntegr. Comp. Physiol., 2006, 290, Rll; R. Bittman, Chem. Phys. Lipids, 2004, 129, 111; S. Brodesser, P. Sawatzki, and T. Kolter, Ear. J. Org. Chem. 2003, 2021.
• J. M. Boggs, W. Gao, and Y. Hirahara, Biochim. Biophys. Acta, 2008, 1780, 445; M. Shimamura, Mini-rev, in Med. Chem., 2008. 8, 285; F. M. Platt, M. Jeyakumar, U. Andersson, R. A. Dwek, and T. D. Butters, Adv. in Exp. Med. Biol., 2005, 564, 1 17; H. Iijima, K. Kimura, T. Sakai, A. Uchimura, T. Shimizu, H. Ueno, T. Natori, and Y. Koezuka, Bioorg. Med. Chem., 1998, 6, 1905.
• T. Hori, M. Sugita, and H. Shimizu, Biochim. Biophys. Acta, Lipid and Lipid Metabolism, 1981, 665, 170; K. Yamada, Yakugaku Zasshi, 2002, 122, 1133.
• K. Motoki, M. Morita, E. Kobayashi, T. Uchida, K. Akimoto, H. Fukushima, and Y. Koezuka, Bio. Pharm. Bull., 1995, 18, 1487; V. Costantino, E. Fattorusso, C. Imperatore, and A. Mangoni, Eur. J. Org. Chem., 2003, 1433.

Terms in the title (1)： 立体