937175-36-5

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 

Downstream Products

• 184914-51-0 [(4R,5R)-5-(3,5-Bis-benzyloxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 
• 352286-65-8 (E)-(S)-3-{4-[3-(3,5-bis-benzyloxy-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester 
• 346600-66-6 C₂₃H₂₂O₃ 

Relevant academic research and scientific papers

Synthesis of catechins via thiourea/AuCl3-catalyzed cycloalkylation of aryl epoxides

(Chemical Equation Presented) A diversity-oriented approach for the synthesis of structurally diverse catechins was achieved in good yields via thiourea/AuCl3/AgOTf-catalyzed annulations of aryl epoxides under mild conditions. This new protocol provides a highly efficient entry to a library of catechins-derived natural products, notably anti-HIV agent 8-C-ascorbyl-(-)-epigallocatechin.

Design of potent PPARα agonists

Computational analysis of the ligand binding pocket of the three PPAR receptor subtypes was utilized in the design of potent PPARα agonists. Optimum PPARα potency and selectivity were obtained with substituents having van der Waals volume around 260. Compound 6 had a PPARα potency of 0.002 μM and a selectivity ratio to PPARγ and PPARδ of 410 and 2000, respectively.

Asymmetric Synthesis of a Series of Chiral AB2 Monomers for Dendrimer Construction

Efficient preparation of a series of four chiral, nonracemic AB2 monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases). Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB2 monomers 1-4 in 57-67% overall yield from 8 and 10.