122885-62-5Relevant academic research and scientific papers
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.
Synthesis of two pairs of enantiomeric C18-sphingosines
Shibuya,Kawashima,Ikeda,Kitagawa
, p. 7205 - 7208 (2007/10/02)
Two pairs of enantiomeric (D-erythro, L-erythro, D-threo, L-threo) C18-sphingosines have been synthesized from Z-butene-1,4-diol utilizing Sharpless asymmetric epoxidation and a regiospecific ring-opening reaction of the resulting C4-chiral epoxide with an azide anion.
SIMULTANEOUS MULTIPLE SYNTHESIS OF PROTECTED PEPTIDE FRAGMENTS ON 'ALLYL'-FUNCTIONALIZED CELLULOSE DISC SUPPORTS
Blankemeyer-Menge, Birgit,Frank, Ronald
, p. 5871 - 5874 (2007/10/02)
The synthesis of several protected peptide fragments on cellulose discs carrying allylic anchor groups is described.The model peptides include the majority of problematic amino acid residues and those types of side chain protecting groups currently used i
