219603-31-3

Upstream product

• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 105452-39-9 (1R,2S)-(+)-2-amino-1-phenyl-1,3-propanediol 
• 99-96-7 4-hydroxy-benzoic acid 
• 78324-14-8 tert-butyldimethylsilyl 4-((tert-butyldimethylsilyl)oxy)benzoate 
• 90446-67-6 4-((tert-butyldimethylsilyl)oxy)benzoyl chloride 
• 1486-51-7 p-(benzyloxy)benzoic acid 
• 219603-30-2 (1R,2S)-(2-(4-((tert-butyldimethylsilyl)oxy)benzamido)-1-phenyl-1,3-propanediyl)bis(4-((tert-butyldimethylsilyl)oxy)benzoate) 
• 219603-32-4 (1R,2S)-(2-(4-(benzyloxy)benzamido)-1-phenyl-1,3-propanediyl)bis(4-(benzyloxy)benzoate) 

Relevant academic research and scientific papers

Synthesis, aggregation, and chiroptical properties of chiral, amphiphilic dendrimers

The syntheses of amphiphilic dendrimers based on 3,5-dihydroxybenzyl alcohol containing tri-or tetrafunctional chiral central cores and allyl ester termini are described. Water solubility is imparted to the dendrimers via a palladium-catalyzed deprotection of the peripheral allyl esters. This method affords complete deprotection of the carboxylate surface because, in contrast to the basic hydrolysis of methyl ester termini, the solubility of partially hydrolyzed intermediates is maintained throughout the course of the deprotection, thereby avoiding precipitation during the reaction. Chiroptical analysis indicates that the structure of the dendrimers collapses in water, resulting in an increased steric effect upon the central core that is manifested by lower optical rotatory power. However, contributions to the chiroptical properties from the dendron branch segments were not evident in water or organic media, suggesting that chiral substructures were not developing in the branch segments of the dendrimers. Multiangle light scattering studies revealed that the dendrimers experienced significant aggregation in aqueous media that decreased at higher generations. This behavior could be rationalized by a change in conformational preference from a disklike conformation at low generations to a more globular conformation at higher generations.

Synthesis and chiroptical properties of dendrimers elaborated from a chiral, nonracemic central core

Three generations of ester-terminated dendrimers have been constructed from (1R,2S)-2-amino-1-phenyl-1,3-propanediol, 1, as the central core. The chiroptical properties of the dendrimers were measured revealing that the molar rotations [Φ] of the dendrimers decreased with increasing dendrimer generation. Comparison to a series of substituted benzoate derivatives of 1 suggested that the decrease in rotation was a consequence of a steric effect upon the conformational equilibrium of the central core that increased with increasing dendrimer generation. The optical rotations of dendrimers 7-9 were also observed to be solvent and temperature dependent.