144879-84-5

Upstream product

• 14218-08-7 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 143-62-4 (+)-digitoxigenin 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 

Downstream Products

• 144879-87-8 14-hydroxy-3β-(tri-O-benzoyl-α-L-rhamnopyranosyloxy)-5β,14β-pregnan-20-one trans-oxime 
• 144879-85-6 14-hydroxy-3β-(tri-O-benzoyl-α-L-rhamnopyranosyloxy)-5β,14β-pregnan-20-one 
• 144879-86-7 3β-(tri-O-benzoyl-α-L-rhamnopyranosyloxy)-5β,14β-pregnane-14,20β-diol 
• 508-93-0 digitoxigenin 3-(α-L-rhamnopyranoside) 
• 145345-82-0 C₄₈H₅₇NO₁₂ 
• 145345-70-6 14-hydroxy-3β-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-21-nor-5β,14β-pregnane-20-carboxaldehyde 
• 188976-60-5 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol 

Relevant academic research and scientific papers

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Synthesis of 20&α- and 20&β-Acetamido, Amino, Nitro and Hydroxy Derivatives of 14-Hydroxy-5&β,14&β-pregnane 3&β-Glycosides: Pregnanes that Bind to the Digitalis Rezeptor

Synthesis of 20α- and 20β-acetamido-, amino-, nitro- and hydroxy-3β-glycoside (α-L-rhamnopyranoside and tris-β-D-digitoxoside) and genin derivatives of 14-hydroxy-5β,14β-pregnane together with the C-20 oxime, hydrazone and amidinohydrazone is described from digitoxin.Ortho esters were also isolated.Structures were established by NMR measurements.These compounds have been shown to bind to the digitalis receptor of heart muscle.The 20β derivatives were consistently more potent than are the corresponding 20α compounds.The 20β-nitro α-L-rhamnoside derivative proved to be the most potent.Receptor binding data are given and structure-activity relationships are presented.