853654-20-3

Upstream product

• 107556-40-1 <4-<<(tert-butyldimethylsilyl)oxy>methyl>phenyl>magnesium bromide 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 873292-73-0 4-(1-methylsilethanyl)benzaldehyde dimethyl acetal 
• 873292-81-0 4-(1-methyl-siletan-1-yl)-benzaldehyde 
• 853654-19-0 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-1-methyl-siletane 

Downstream Products

• 853654-23-6 1-[4-(4-methoxy-phenoxymethyl)-phenyl]-1-methyl-siletane 
• 853654-21-4 1-(4-bromomethyl-phenyl)-1-methyl-siletane 
• 853654-24-7 1-methyl-1-[4-(3-phenyl-propoxymethyl)-phenyl]-siletane 
• 853654-22-5 1-[4-(biphenyl-4-yloxymethyl)-phenyl]-1-methyl-siletane 
• 853654-25-8 1-methyl-1-[4-(1-phenyl-ethoxymethyl)-phenyl]-siletane 
• 775356-24-6 4-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-phenol 
• 853654-27-0 4-(3-phenyl-propoxymethyl)-phenol 
• 853654-28-1 4-(1-phenyl-ethoxymethyl)-phenol 

Relevant academic research and scientific papers

New reagents for the synthesis of arylmethyl ethers and esters

This Account chronicles efforts leading up to the development of new arylmethyl transfer (benzylation) reagents for protecting oxygen functional groups under relatively mild and neutral conditions. It begins with an investigation of organosiletanes as surrogate hydroxyl groups, which inspired siletane-functionalized benzyl ethers and forced us to confront the difficulties associated with the synthesis of benzyl ethers. The end result is a new series of neutral oxypyridinium salts for the benzylation of various nucleophilic functional groups under mild conditions. 1 Introduction 2 Tamao-type Oxidation of Strained Organosiletanes 3 p-Siletanylbenzyl (PSB) Protecting Groups 4 2-Benzyloxy-1-methylpyridinium Triflate 5 Friedel-Crafts Reactions and Mechanistic Insights 6 Benzyl Ester Formation 7 Substituted Benzyl Transfer Reagents 8 Conclusions and Outlook. Georg Thieme Verlag Stuttgart New York.

New strategies for protecting group chemistry: Synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers

Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The parasiletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions-involving alkaline hydrogen peroxide - that are unique among cleavage protocols for arylmethyl ethers. Furthermore, the PSB group affords the user new flexibility in the implementation of protecting group strategies that revolve around multiple arylmethyl ether protecting groups. In addition to hydrogen peroxide-based cleavage protocols, conversion of a PSB ether into a para-methoxybenzyl (PMB) ether and assembly of a PSB ether from a pre-existing para-bromobenzyl (PBB) ether are described. Finally, a new reagent for installing PSB ethers under neutral "mix and heat" conditions is reported.

p-siletanylbenzylidene acetal: Oxidizable Protecting group for diols

Hydrogen peroxide oxidation of benzylidene acetals (and derivative benzyl ethers) that incorporate a siletane ring at the para position creates a deprotection pathway without affecting other important chemical properties of the benzylidene acetal, such as

The para-siletanylbenzyl (PSB) ether: A peroxide-cleavable protecting group for alcohols and phenols

A novel arylmethyl protecting group that is electronically similar to benzyl (Bn) but that can be cleaved under mild oxidizing conditions in the presence of para-methoxybenzyl (PMB) is described herein. para-Siletanylbenzyl (PSB) ethers are formed in one or two steps from the corresponding alcohols and cleaved in one or two steps with basic peroxide. Alcohols and phenols have been protected in good yields and deprotected cleanly under mild oxidative conditions.