218937-73-6

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 67-56-1 methanol 
• 294637-30-2 6-O-(4-chlorobenzyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 105-13-5 4-Methoxybenzyl alcohol 
• 1616487-09-2 4-methoxybenzyl N-allyl thiocarbamate 
• 220235-77-8 4-methoxybenzyl-2-pyridylthio carbonate 

Downstream Products

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant academic research and scientific papers

P-chlorobenzyl ether: A p-methoxybenzyl ether in disguise

In the chemistry of polyfunctionalized organic compounds, protecting groups that can undergo mild and selective cleavage while still being stable during the entire synthetic sequence are often required. In this work, we present a straightforward conversion of the robust p-chlorobenzyl ether into the more labile and well-described p-methoxybenzyl ether using palladium catalysis. This reaction was demonstrated to be high yielding and compatible with a wide range of functionalities, thereby providing a useful supplement to the conventional ether protecting groups.

Simple and efficient method for the protection of hydroxyl groups as 4-methoxybenzyl ethers

PMB ethers of alcohols are obtained in good yields and under mild conditions using the 4-methoxybenzyl N-allyl thiocarbamate and N-bromosuccinimide (NBS)/TfOH as the catalyst. The present method is very fast, simple, and efficient. Copyright

Zirconium(IV) chloride catalyzed new and efficient protocol for the selective cleavage of p-methoxybenzyl ethers

A highly selective and efficient method for the unmasking of p-methoxybenzyl (PMB) ethers and esters has been developed by use of 20 mol % of zirconium(IV) chloride as Lewis acid in acetonitrile. The present method is very fast, and the conditions are tolerable to a variety of acid/ base-sensitive protecting groups and substrates such as carbohydrates, terpenes, and amino acids. The products are obtained in good to high yields.

Solution and solid phase p-alkoxybenzylation of alcohols under neutral conditions

Primary, secondary, and tertiary alcohols can be converted to p- methoxybenzyl ethers under neutral conditions in the presence of a variety of commonly used functional and protective groups. The method can be adapted to solid phase on a Wang resin.