35017-04-0Relevant articles and documents
Synthesis of the mixed acetal segment of S-glyceroplasmalopsychosine
Parhi, Ajit K.,Mootoo, David R.,Franck, Richard W.
scheme or table, p. 9821 - 9827 (2009/04/03)
In this report the concept of converting carbohydrate to non-carbohydrate asymmetric molecules has been successfully exploited. The mixed acetal segment of glyceroplasmalopsychosine, a novel glycolipid, has been synthesized in a stereospecific manner using two simple sugar units. The glycosidation reaction between these two monosaccharides ensured the correct acetal stereocenter of the target molecule. Either olefin metathesis or heterogeneous Wittig reactions were used for constructing the long aliphatic chain of glyceroplasmalopsychosine.
SYNTHESIS OF 6-O-(5-ACETAMIDO-3,5-DIDEOXY-α-D-glycero-D-galacto-2-NONULOPYRANOSYLONIC ACID)-D-GALACTOSE
Vleugel, Dominicus J. M. van der,Wassenburg, Fred R.,Zwikker, Jan W.,Vliegenthart, Johannes F. G.
, p. 221 - 234 (2007/10/02)
Condensation of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate with benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside, using silver salicylate as promoter, gave benzyl 2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)-β-D-galactopyranoside (11) as the main product in 65percent yield.Furthermore, the following by-products were formed: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-salicyloyl-D-glycero-D-galacto-2-nonulopyranosonate, methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enopyranosonate, and an impure compound that gave, after O-deacetylation and catalytic hydrogenolysis, 6-O-(methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosylonate)-D-galactose.O-Deacetylation of 11 gave benzyl 2,3,4-tri-O-benzyl-6-O-(methyl 5-acetamido-3,5-dideoxy-α-D-glycro-D-galacto-2-nonulopyranosylonate)-β-D-galactopyranoside, which was converted into 6-O-(methyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)-D-galactose (13) by catalytic hydrogenolysis.Saponification of 13 gave the title compound as its potassium salt.