129779-76-6Relevant academic research and scientific papers
Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000
Leung, Leo,Tomassi, Cyrille,Van Beneden, Katrien,Decruy, Tine,Elewaut, Dirk,Elliott, Tim,Al-Shamkhani, Aymen,Ottensmeier, Christian,Van Calenbergh, Serge,Werner, Joern,Williams, Tony,Linclau, Bruno
supporting information; experimental part, p. 4433 - 4436 (2009/05/26)
(Chemical Equation) The synthesis of 4-deoxy-4,4-difluoro-KRN7000 starting from phytosphingosine is described. Key steps include a regioselective benzylation of azidophytosphingosine and a deoxofluor-mediated fluorination of the corresponding 4-ketone. Th
Structure-activity relationship of α-galactosylceramides against b16- bearing mice
Morita,Motoki,Akimoto,Natori,Sakai,Sawa,Yamaji,Koezuka,Kobayashi,Fukushima
, p. 2176 - 2187 (2007/10/02)
Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.
Total Synthesis of (2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate, a Partially Protected Ceramide Part of Sponge Cerebrosides
Nakashima, Hideki,Hirata, Norihiko,Iwamura, Takeru,Yamagiwa, Yoshiro,Kamikawa, Tadao
, p. 2849 - 2858 (2007/10/02)
(2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, apertially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined.The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.
Total Synthesis of (2S,3S,4R)-N-Tetracosanoyl-2-amino-1,3,4-octadecanetriol, a Ceramide Part of Wheat Flour Glycosyl Ceramides
Koike, Katsuya,Nakahara, Yoshiaki,Ogawa, Tomoya
, p. 663 - 667 (2007/10/02)
The synthesis of (2S,3S,4R)-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol (5) was achieved in eight steps in a 23 percent overall yield starting from 3,4,6-tri-O-benzyl-D-galactopyranose (6), and then ceramide 5 was converted to (2S,3S,4R)-3,4-di-O-benzoy
