Glycosphingolipid

MELTING POINT	:
BOILING POINT	:
REFRACTIVE INDEX	:
OPTICAL ROTATION	:	+11.3(Ref. 3010)
DENSITY	:
SOLUBILITY	:

UV SPECTRA	:
IR SPECTRA	:
NMR SPECTRA	:	1D 1H-NMR (Ref. 3010)
MASS SPECTRA	:
OTHER SPECTRA	:

Chemical Synthesis

Coupling of 2- (trimethylsilyl)ethyl O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3',4'-O-isopropylidenation, O-benzylation, and subsequent removal of the isopropylidene group, with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate using N-iodosuccinimide (NIS), gave the trisaccharide), which on condensation with methyl 6-O-benzoyl -2-deoxy-3,4-O-isopropylidene-2-phthalimido-1-thio-b-D-galactopyranoside , gave the protected ganglioside GM2 oligosaccharide.
This was transformed, via O-deisopropylidenation, O-acetylation, removal of the phthaloyl group, N-acetylation, removal of the benzyl groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the final glycosyl donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with the a-trichloroacetimidate gave the b-glycoside, which on channeling through selective reduction of the azide group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title ganglioside. (Ref. 3010)

Fatty acid C18:0

LCB d18:1

[3010]

AUTHOR	:	Hasegawa, A., Nagahama, T., Ohki, H., and Kiso, M.
TITLE	:	A facile total synthesis of ganglioside GM2.
JOURNAL	:	Journal of Carbohydrate Chemistry
VOL	:	11 PAGE : 699 -714 (1992)

---