143544-19-8Relevant academic research and scientific papers
Sphingolipids and glycerolipids. IV. Syntheses and ionophoretic activities of several analogues of soya-cerebroside II, a calcium ionophoretic sphingoglycolipid isolated from soybean
Shibuya,Kurosu,Minagawa,Katayama,Kitagawa
, p. 1534 - 1544 (2007/10/02)
For examination of the structure-activity relationship five analogues [(2'R)-2'-hydroxypalmitoyl (3), palmitoyl (4), (2'S)-2'-hydroxypalmitoyl (5), β-D-galactosyl (6), and 8,9-dihydro (7) relevancies] of soya-cerebroside II (2), which is a calcium ionopho
Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside
Shibuya,Kawashima,Narita,Ikeda,Kitagawa
, p. 1154 - 1165 (2007/10/02)
Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.
