Fw. Lichtenthaler et al., PRACTICAL SYNTHESIS OF TA-D-XYL-(1-]2)-BETA-D-MAN-(1-]4)-ALPHA-D-GLC-OME, A TRISACCHARIDE COMPONENT OF THE HYRIOPSIS-SCHLEGELII GLYCOSPHINGOLIPID, Journal of organic chemistry, 59(22), 1994, pp. 6735-6738
By employing the readily accessible (preceding paper in this issue) 3,
4,6-tri-O-benzyl-alpha-D-arabino-hexosyl bromide (1) as an indirect, b
eta-specific mannosyl donor, a practical three-step synthesis was elab
orated for methyl xylosyl-beta(1-->2)-mannosyl-beta(1-->4)-glucoside (
11), a trisaccharide component of Hyriopsis schlegelii ceramide oligos
accharides. Key steps were the silver aluminosilicate-induced, beta-sp
ecific glycosidation of 1 with methyl 2,3,6-tri-O-benzyl-alpha-D-gluco
side and the silver triflate-promoted beta-xylosylation with 2,3,4-tri
-O-benzoyl-alpha-D-xylosyl bromide. The overall yield amounted to a sa
tisfactory 47%.