128802-69-7Relevant academic research and scientific papers
Synthesis of a hematoside analog containing phytosphingosine and α-hydroxfatty acid
Sugata, Tetsuji,Kan, Yoko,Nagaregawa, Yoshiteru,Miyamoto, Tomofumi,Higuchi, Ryuichi
, p. 917 - 925 (2007/10/03)
The hematoside analog 1 [NeuGcα(2→3)Galβ(1→4)Glcβ(1→1)Cer], which contains a phytosphingosine as a sphingoid base and an α-hydroxyfatty acid, has been synthesized. Coupling of the methyl (methyl 5-benzyloxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero- α-and -β-D-galacto-2-nonulopyranosid)onate 5, prepared from the corresponding 5-acetamido derivative 2, with a lactose derivative 6 afforded sialolactoside 7, which was converted to the corresponding trichloroacetimidate 10. Glycosylation of 10 with the ceramide tribenzoate 12 gave the protected hematoside analog 13, which was deprotected to the hematoside analog 1.
Biologically Active Glycosides from Asteroidea, XXVI. Stereochemistry of the Four Diastereomers of Ceramide and Ceramide Lactoside
Sugiyama, Shigeo,Honda, Masanori,Higuchi, Ryuichi,Komori, Tetusya
, p. 349 - 356 (2007/10/02)
The diastereomeric ceramides, (2S,3S,4R)-, (2S,3S,4S)-, (2S,3R,4S)-, and (2S,3R,4R)--1,3,4-hexadecanetriols 5-8 and the corresponding ceramide lactosides 1-4 have been synthesized.Compound 1 is almost identical with the natural specimen, acanthalactoside A.The physical data of these diasteromeric compounds are most useful to determine the stereochemistry of ceramides and ceramide lactosides, either isolated from natural sources or obtained by partial hydrolysis of gangliosides.
Biologically Active Glycosides from Asteroidea, XXIII. Synthesis of Acanthacerebroside A
Sugiyama, Shigeo,Honda, Masanori,Komori, Tetsuya
, p. 1063 - 1068 (2007/10/02)
(R)-2-Hydroxytetracosanoic acid (2), prepared by using the chiral building block benzyl (R)-2,3-epoxypropyl ether (7), was coupled to (2S,3S,4R)-2-amino-1,3,4-hexadecanetriol (3) to give the ceramide 4.Glycosidation of 4 with D-glucopyranose affords acant
