543698-59-5

Upstream product

• 475650-92-1 (-)-6-O-allyl-2-O-hexadecanoyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol 
• 475650-90-9 C₃₇H₄₄O₇ 
• 158110-45-3 (-)-3,4-di-O-benzyl-1,2:5,6-di-O-cyclohexylidene-myo-inositol 
• 475650-91-0 (+)-6-O-allyl-1-O-(p-methoxybenzyl)-4,5-di-O-benzyl-myo-inositol 
• 151426-85-6 (-)-6-O-allyl-3,4-di-O-benzyl-1,2-O-cyclohexylidene-myo-inositol 
• 475650-94-3 6-O-acetyl-4-O-allyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranosyl fluoride 
• 13265-84-4 D-glucal 
• 211869-78-2 6-O-allyl-1-O-(p-methoxybenzyl)-2,3:4,5-di-O-cyclohexylidene-myo-inositol 
• 211799-72-3 (-)-6-O-allyl-1-O-(p-methoxybenzyl)-2,3-O-cyclohexylidene-myo-inositol 
• 211869-77-1 (+)-6-O-allyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol 
• 145843-68-1 (+)-6-O-butyryl-2,3:4,5-di-O-cyclohexylidene-myo-inositol 
• 154372-20-0 1D-6-O-allyl-3,4,5-tri-O-benzyl-1-O-(4-methoxybenzoyl)-myo-inositol 
• 154372-19-7 C₃₆H₄₂O₆ 
• 154459-81-1 (-)-6-O-allyl-3,4,5-tri-O-benzyl-myo-inositol 

Relevant academic research and scientific papers

First total synthesis of a GPI-anchored peptide

A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoeth-anolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.

Convergent Synthesis of a GPI Containing an Acylated Inositol

A GPI of sperm CD52 was synthesized by a highly convergent procedure, representing the first chemical synthesis of a complex GPI having an acylated inositol. The presence of a large acyl group resulted in unusual properties and reactions of the relevant intermediates, which gave rise to a number of problems. To overcome the problems and achieve the target molecule, a new synthetic strategy was developed. First, the pseudodisaccharide of 2-O-palmitoylinositol was phospholipidated, and then the trimannose segment and the phosphoethanolamine group were sequentially attached. Global deprotection eventually afforded the sperm CD52 GPI. The method may be useful for the synthesis of other GPIs having an acylated inositol.