125289-66-9

Upstream product

• 61493-53-6 ethyl 3-[4-(3-methyl-but-2-enyloxy)phenyl]-propionate 
• 23795-02-0 3-(4-hydroxy-phenyl)-propionic acid ethyl ester 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 410087-93-3 3-methyl-2-butenyl 3-[4-(3-methyl-2-butenyloxy)-phenyl]propyl ether 
• 870-63-3 prenyl bromide 

Downstream Products

• 51593-96-5 4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol 
• 130487-28-4 3--1-propanol 
• 130487-29-5 (E)-3--1-propanol 

Relevant academic research and scientific papers

Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist

A series of 29 oxyprenylated and azoprenylated phenylpropanoids were chemically synthesized and tested in transfected cultured HepG2 cells by means of the dual-luciferase assay as farnesoid X receptor (FXR) agonists, using the endogenous ligand chenodeoxy

The prenyl group: A versatile hydroxy protecting group, removable chemoselectively under mild conditions

Iodine in dichloromethane (in the presence of 3? molecular sieves for acid-sensitive substrates) and 2,3-dichloro-5,6-dicyanoquinone (DDQ) in dichloromethane-water (9:1) are mild and efficient methods to cleave prenyl ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, allyl, benzyl and TBDPS groups. Exposure of aryl prenyl ethers to iodine led to the formation of 3-iodo-2,2-dimethylchroman derivatives in acceptable yields via a tandem Friedel-Crafts/iodocyclization reactions. Facile one-step transformation of two iodinated dimethylchroman derivatives allowed the synthesis of natural flavanoids among them: zanthoxylol, an anti-sickling agent.

An efficient and chemoselective cleavage of prenyl ethers with DDQ

The prenyl (Pre) protecting group tor hydroxyl functions is readily removed at room temperature with DDQ in dichloromethane-water (9:1). The reaction conditions are compatible with the presence of other ethereal functionalities such as acetonides, allyl, benzyl, TBS, TBDPS groups. We have also shown that Sdeprotection of prenyl ethers using a catalytic amount of DDQ in the presence of 3 equivalents of Mn(OAc)3 is a good alternative for the use of a stoichiometric amount of DDQ, albeit the reaction time being longer.