Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO4

• Published in: Journal of organic chemistry Vol. 70; no. 18; pp. 7196 - 7207
• Main Authors: HEDEROS, Markus, KONRADSSON, Peter
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.09.2005; Amer Chemical Soc
• Subjects: Animals; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Exact sciences and technology; Glycolipids - chemical synthesis; Organic chemistry; Phospholipids - chemical synthesis; Physical Sciences; Preparations and properties; Science & Technology; Trypanosoma cruzi - chemistry; ALLYL ETHERS; PHOSPHONATE; SERINE; ISOMERIZATION; PHOSPHATES; FRAGMENT; CERAMIDE; GLYCAN; CATIONIC IRIDIUM COMPLEX; EFFICIENT; Kinetoplastida; Protozoa; Phosphoinositide; Organic azide; Lipids; Myo stereoisomer; Complex lipid; Glycolipid; Trypanosoma cruzi; Amine; Glycophospholipid; Chemical synthesis; Tetrasaccharide
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0508595

Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.