Carbohydrates in diversity-oriented synthesis: challenges and opportunities

2016 ◽  
Vol 14 (3) ◽  
pp. 808-825 ◽  
Author(s):  
E. Lenci ◽  
G. Menchi ◽  
A. Trabocchi
Keyword(s):  
Functional Groups ◽  
Building Blocks ◽  
High Density ◽  
Diversity Oriented Synthesis ◽  
Challenges And Opportunities ◽  
Polar Functional Groups

Carbohydrates are attractive building blocks for diversity-oriented synthesis due to their stereochemical diversity and high density of polar functional groups.

A Practical and General Approach to the Late-Stage Functionalization of Complex Sulfonamides

2019 ◽  
Author(s):  
Patrick Fier ◽  
Kevin M. Maloney
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Building Blocks ◽  
Pharmaceutical Compounds ◽  
Stage Conversion

Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed <i>N</i>-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. Based on the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.

A Practical and General Approach to the Late-Stage Functionalization of Complex Sulfonamides

2019 ◽  
Author(s):  
Patrick Fier ◽  
Kevin M. Maloney
Keyword(s):  
Functional Groups ◽  
Late Stage ◽  
Building Blocks ◽  
Pharmaceutical Compounds ◽  
Stage Conversion

Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed <i>N</i>-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. Based on the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

A Study of Surface Modification on Adsorption Behaviors of Nanoporous Carbon

2007 ◽  
Vol 119 ◽  
pp. 211-214 ◽  
Author(s):  
Byeoung Ku Kim ◽  
Young Seak Lee ◽  
Seung Kon Ryu ◽  
Byung Joo Kim ◽  
Soo Jin Park
Keyword(s):  
Nitric Acid ◽  
Functional Groups ◽  
Carbon Fibers ◽  
Acid Treatment ◽  
Surface Acidity ◽  
Activated Carbon Fibers ◽  
Adsorption Behaviors ◽  
Toxic Gases ◽  
Adsorption Amount ◽  
Polar Functional Groups

In this work, to introduce polar functional groups on carbon surfaces, activated carbon fibers (ACFs) were treated by nitric acid in order to enhance the adsorption capacity of propylamine which was one of toxic gases in cigarette smoke. It was found that the polar functional groups were predominantly increased up to 2.0 M of nitric acid, resulting in the increase of total surface acidity. It was found that the adsorption amount of propylamine of the modified ACFs was increased around 17% after a nitric acid treatment. From the XPS results, it was observed that propylamine was reacted with strong or weak polar (acidic) groups, such as COOH, -COO or OH existed on the ACF surfaces.

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

Surface Modification of Asymmetric Polysulfone Membrane by UV Irradiation

2014 ◽  
Vol 70 (2) ◽  
Author(s):  
Sutthisa Konruang ◽  
Thawat Chittrakarn ◽  
Suksawat Sirijarukul
Keyword(s):  
Contact Angle ◽  
Surface Modification ◽  
Functional Groups ◽  
Uv Irradiation ◽  
Water Flux ◽  
Inversion Method ◽  
Asymmetric Structure ◽  
Polysulfone Membrane ◽  
Polar Functional Groups ◽  
Polysulfone Membranes

The effects of ultraviolet (UV) irradiation for surface modification of hydrophobic asymmetric polysulfone membranes have been investigated. The asymmetric polysulfone (PSF) membranes were prepared by phase inversion method using 19%-25% of PSF in two solvents, viz. dimethylacetamide (DMF) and Acetone (Ac) collectively. The surface of asymmetric polysulfone membranes were modified by UV ray with 254 and 312 nm wavelength. Chemical and physical properties of the untreated and the treated membranes were characterized. Scanning electron microscope (SEM) was used to determine asymmetric structure of polysulfone membranes. Contact angle device was used to analyzed the effected of UV ray treatment on hydrophilicity of membranes surface. Polar functional groups introduced by UV irradiation were examined using FTIR. The water flux was measured under a pressure of 500 kPa to 2,500 kPa with a feed temperature of 25°C. It was shown that asymmetric polysulfone membranes were produced and the UV ray treatment significantly alters the hydrophilicity of membranes surface indicated by the reduction of water contact angle with increasing treatment time. The FTIR analysis showed the formations of polar functional groups such as hydroxyl and carbonyl groups. Consequently, the surface of asymmetric polysulfone membranes was changed from hydrophobic to hydrophilic by UV irradiation leading to the enhancement of the water flux.

scholarly journals Self assembled nanocages from DNA–protoporphyrin hybrid molecules

RSC Advances ◽  
2015 ◽  
Vol 5 (108) ◽  
pp. 89025-89029 ◽  
Author(s):  
Vandana Singh ◽  
Mohan Monisha ◽  
Roy Anindya ◽  
Prolay Das
Keyword(s):  
Functional Groups ◽  
Protoporphyrin Ix ◽  
Building Blocks ◽  
Carboxyl Groups ◽  
Dna Oligomers ◽  
Organic Hybrid ◽  
Molecular Building Blocks ◽  
Modified Dna ◽  
Hybrid Molecules ◽  
Self Assembled

DNA–organic hybrid molecular building blocks are generated by covalent conjugation of the carboxyl groups of protoporphyrin IX with the amine functional groups of modified DNA oligomers.

A Chiral Interlocking Auxiliary Strategy for the Synthesis of Mechanically Planar Chiral Rotaxanes

2021 ◽  
Author(s):  
Alberto de Juan ◽  
David Lozano ◽  
Andrew Heard ◽  
Michael Jinks ◽  
Jorge Meijide Suarez ◽  
...  
Keyword(s):  
Functional Groups ◽  
Direct Synthesis ◽  
Building Blocks ◽  
Bond Forming ◽  
Single Target

We have serendipitously discovered a combination of reaction partners that function as a “chiral interlocking auxiliary” to both orientate a macrocycle and, effectively, load it onto a new axle. We demonstrate the potential of this finding through the synthesis of a number of targets in high enantiopurity, without separation of stereoisomers, including examples whose axles lack any functional groups that would allow their direct synthesis by other means, so called “impossible” rotaxanes. Intriguingly, by varying the order of bond forming steps, we can effectively choose which end of an axle the macrocycle is loaded onto, allowing the synthesis of both hands of a single target using the same reactions and building blocks.

scholarly journals Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 454-458 ◽  
Author(s):  
Danny Ho ◽  
Jonas Calleja ◽  
Matthew Gaunt
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Building Blocks ◽  
Activation Pathway ◽  
Bond Forming ◽  
Aliphatic Ketones ◽  
Palladium Catalyzed

A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles.

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