Reductive Radical Cascades Triggered by Alkoxyl Radicals in the β-Cyclodextrin Framework

Organic Letters
Elisa I LeónErnesto Suárez

Abstract

The generation and fate of 2I-VII,3I-VII,6II-VII-icosa- O-methyl-β-cyclomaltoheptaos-6I- O-yl radical under reductive conditions is described. Two radical cascade reactions are involved: the main one is triggered by a 1,8-HAT of the hydrogen at 5VIIC. The radical can reach the anomeric hydrogen at 1VC three sugar units ahead using a six-step sequence. The different hydrogen donor ability of the group 14 hydrides permits one to selectively stop the cascade at 5VIIC, 2VIC, and 4VIC to obtain β-CD with a β-l-Ido p unit, acyclic hepta-, and hexa-saccharide structures, respectively.

References

Feb 19, 2002·Chemical Reviews·Giuseppe GattusoJ. Fraser Stoddart
Nov 16, 2002·Angewandte Chemie·Rachel ChuardPhilippe Renaud
Nov 16, 2002·Angewandte Chemie·Rachel ChuardPhilippe Renaud
Feb 11, 2004·Organic & Biomolecular Chemistry·W Russell BowmanMark B Schilling
Mar 10, 2006·Organic Letters·Edelmiro MomanAntonio Mouriño
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
Jan 1, 2008·Chemistry : a European Journal·Chryssostomos Chatgilialoglu
Oct 16, 2008·Organic Letters·Maria ZlotorzynskaGlenn M Sammis
Mar 5, 2014·Organic & Biomolecular Chemistry·Julio Rodríguez-LavadoJosé M García Fernández
Oct 28, 2014·Chemistry : a European Journal·Malek NechabMichèle P Bertrand
Jan 24, 2015·Organic & Biomolecular Chemistry·Sergey VolkovTomáš Kraus
Jan 30, 2015·Angewandte Chemie·Dimitri Alvarez-DortaErnesto Suárez
May 23, 2015·The Journal of Organic Chemistry·Stéphane MenuelFrédéric Hapiot
Jan 23, 2016·Chemical Society Reviews·R ArdkheanE A Anderson
Sep 16, 2016·Journal of the American Chemical Society·Ming YanPhil S Baran
Nov 3, 2016·The Journal of Organic Chemistry·Dimitri Alvarez-DortaErnesto Suárez
Feb 9, 2017·Journal of Medicinal Chemistry·M Isabel García-MorenoCarmen Ortiz Mellet
Apr 24, 2018·The Journal of Organic Chemistry·Tania NevaJosé M García Fernández

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.