Skip to Content
Merck
HomeProductsChemistry & BiochemicalsChemical SynthesisProtection/Deprotection Reagents

Protection/Deprotection Reagents

2-Benzyloxy-1-methylpyridinium triflate: an air-stable pre-activated pyridinium salt for the mild benzylation of alcohols under neutral conditions

One of the common difficulties with natural product and other multi-step syntheses is the need to render one functional group inert to a particular reagent, while keeping another group open for further chemical elaboration. Despite the great advances made in the involved synthesis of multifunctional products, chemoselectivity in functional group transformations remains a critical issue in organic synthesis. Unfortunately, there is no perfect protecting group applicable to any functional group in any situation. Thus, the chemist needs a handy toolbox of selective and efficient protection reagents that can be applied and easily removed under a variety of conditions by a deprotection reagent.   

Read more

We are pleased to offer an unmatched portfolio of alcohol protecting groups, amine protecting groups, carbonyl protecting groups, carboxylic acid protecting groups, phosphate protecting groups, and terminal alkyne protecting groups to make your breakthroughs feel closer than ever. Selected highlights are:

  • The Dudley Reagent is capable of benzylation of alcohols under neutral conditions. Allyl and 4-methoxybenzyl trichloroacetimidates are also commonly used to protect alcohols in various synthetic applications.
  • Ethynylnaphthalenes offer sterically unobtrusive protection of hydroxyl groups on carbohydrates with orthogonal reactivity compared to benzyl ethers.
  • The (2-trimethylsilyl)ethanesulfonyl (SES) group is used to protect amines via SES chloride; alternatively, SES-NH2 can be used to introduce a SES-protected amine functionality directly into a molecule.
  • The Heller-Sarpong reagents promote highly chemoselective esterification and amidations as a practical alternative to diazoalkanes and Weinreb amide protocols.
  • Our fluorous protecting groups serve several purposes, acting as protecting groups and serving as temporary fluorous tags that can facilitate product design and purification throughout a synthesis.

It is equally important to be able to remove the protecting group at the end of the synthesis. Our portfolio of deprotecting agents will help you get to your desired molecule to reach new scientific frontiers.

Related Product Resources

Brochure: ChemFiles - Protection

Related Product Categories
Transition Metal Catalysts
Discover our unparalleled portfolio of transition metal catalysts for your different organic and organometallic chemistry-based applications.
Organocatalysts
Stock your green chemistry toolbox with our exceptional portfolio of organocatalysts for sustainable synthesis of complex molecules in small molecule drug discovery.
Inorganic Catalysts
Explore our unparalleled portfolio of common heterogeneous/inorganic catalysts such as platinum, palladium, ruthenium, and rhodium supported on porous carbon or silica.
Fluorinated Building Blocks
With a vast offering of fluorinated building blocks, such as, trifluoromethyl, difluoromethyl, triflate, and pentafluorosulfanyl substituents for your toolkit, we make it even easier to discover your target compounds.
Halogenated Heterocycles
Shop our diverse portfolio of halogenated heterocycles for use in a vast array of synthetic protocols, including lithiation and palladium catalyzed cross-coupling methodologies.
Halogenation Reagents
Enhance research success with diverse halogenated substrates for bromination, chlorination, fluorination, haloboration and iodination, for many synthessis stages.
Related Applications
C–H Functionalization
C–H functionalization is the reliable and predictable conversion of a C–H into a C–C, C–N, C–O, or C–X bond in a selective and controlled fashion.
Cross-Coupling
Cross-coupling is a common reaction in organic chemistry for the creation of C-C, C-N, and C-O bonds with the aid of a metal catalyst.
Fluorination
Fluorination is the introduction of fluorine to a compound via electrophilic fluorination, nucleophilic fluorination, difluoromethylation, trifluoromethylation, or perfluoroalkylation.
Metathesis
Olefin metathesis involves an organic reaction that redistributes fragments of alkenes (olefins) by cleavage and transformation of carbon-carbon double bonds.
Photocatalysis
Photoredox catalysis utilizes photocatalysts in the presence of visible light to form an array of synthetic transformations including, but not limited to, cross-coupling, C-H functionalization, alkene and arene functionalization, and trifluoromethylation.
Organic Reaction Toolbox
An organic reaction toolbox provides structure-activity relationships for unique chemical reactions to optimally design and control small molecule synthesis.
RELATED SERVICES
SYNTHIA™ Retrosynthesis Software
Our custom cell culture product design experts can offer advice and support as you scale your bioprocess from clinical to commercial supply, assisting with liquid products, dry powder products, selection of raw materials, quality testing, flexible product packaging, and product documentation.
Bulk and Custom Services
We offer an extensive, reliable supply of production materials in bench to bulk volumes. Our custom services include quality control, testing, documentation services, chemical packaging, contract manufacturing according to your specifications.
Small Molecule Library Design (Aldrich Market Select)
Streamline the management of your screening compounds with our Aldrich Market Select online order center for small molecule libraries, comprising over 14 million chemistry building blocks and other useful services.
Sign In To Continue

To continue reading please sign in or create an account.

Don't Have An Account?