Cyanomethyl (CNMe) ether: an orthogonal protecting group for saccharides
Mosidur Rahaman Molla1, Rima Thakur1
1National Institute of Technology Patna, Ashok Rajpath, Patna 800005, India. rima@nitp.ac.in.
Abstract:
Logical manipulation of protecting groups is one of the vital strategies involved in the synthesis of complex oligosachharides. As opposed to the robust permanent protecting groups, the chemoselective protection-deprotection processes on orthogonal protecting groups have facilitated the synthesis of the target molecules with higher effeciency. While the derivatives of benzyl ethers are the most popular orthogonal ether based protecting groups for hydroxyls, the exploration of methyl ethers for similar synthetic application is much limited. We herein report cyanomethyl (CNMe) ether as a readily synthesized orthogonal protecting group for saccharides. The ether moiety was rapidly removed under Na-naphthalenide conditions in good to excellent yields and was found to be compatible with other well-known benzyl/methyl/silyl ether and acetal protecting groups. Additionally, the CNMe group was observed to be tolerant to standard reagents used for the deprotection of ether, ester and acetal protecting groups. The protection and deprotection steps remained unaffected by the position of hydroxyl, the configuration of monosaccharides or the presence of olefins in the skeleton.
Related Concept Videos
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Protecting Groups for Aldehydes and Ketones: Introduction
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
Naming Enantiomers
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3


