Synthesis of CH2 -Linked α(1,6)-Disaccharide Analogues by α-Selective Radical Coupling C-Glycosylation

Organic Letters
Noriaki KiyaGo Hirai

Abstract

C-Linked carbohydrate structure, in which the cleavable O-glycosidic linkage is replaced by a carbon unit, is a useful tool for functional analyses of glycoconjugates. We describe a synthetic method for α-CH2-linked disaccharide structures, such as Glc(1,6)-Glc, by stereoselective radical-coupling C-glycosylation between a conformationally constrained and stable C1-sp3 hybridized xanthate donor and a carefully designed acceptor.

References

Mar 28, 2001·Science·C R Bertozzi, L L Kiessling
Mar 8, 1996·The Journal of Organic Chemistry·William R. KobertzMark D. Bednarski
Mar 28, 1996·Chemical Reviews·Raymond A. Dwek
Nov 7, 2002·Current Genetics·Naoki KatoNorihiro Tsukagoshi
Mar 20, 2003·Chemistry : a European Journal·Lutz F TietzeAlessandro Dondoni
Aug 21, 2003·Organic & Biomolecular Chemistry·Sara PalmierJean-Marie Beau
May 11, 2004·Cancer Science·Reiji KannagiNaoko Kimura
Oct 9, 2004·The Journal of Organic Chemistry·Jared L Piper, Maarten H D Postema
Dec 9, 2004·Chemical Reviews·Raz Jelinek, Sofiya Kolusheva
Dec 6, 2005·Organic & Biomolecular Chemistry·Alejandro Cordero-VargasSamir Z Zard
Apr 27, 2007·Nature·Peter H Seeberger, Daniel B Werz
Aug 4, 2007·Organic Letters·Nadège Lubin-GermainJacques Augé
Nov 24, 2007·Journal of the American Chemical Society·Go HiraiMikiko Sodeoka
Feb 7, 2008·Organic Letters·Nadège Lubin-GermainJacques Augé
Aug 7, 2010·Organic Letters·Dennis C KoesterDaniel B Werz
Jul 26, 2011·Chemical Communications : Chem Comm·Shino ManabeYukishige Ito
Sep 10, 2013·Chemistry : a European Journal·Sachin B NaruteChepuri V Ramana
Nov 26, 2013·Organic Letters·Laurent DebienSamir Z Zard
Jan 16, 2015·ACS Medicinal Chemistry Letters·Mingzong LiGeorge A O'Doherty
Feb 1, 2015·Blood Reviews·Siobhan V GlaveyMichael E O'Dwyer
Mar 25, 2015·Chemistry : a European Journal·Beata OroszovaKamil Parkan
Jun 22, 2016·Organic & Biomolecular Chemistry·Samir Z Zard
Sep 16, 2017·Chemical Reviews·You Yang, Biao Yu
May 1, 1996·Chemistry : a European Journal·Hansjörg StreicherRichard R Schmidt
Feb 22, 2018·Organic & Biomolecular Chemistry·Hongze LiaoXue-Wei Liu
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo

❮ Previous
Next ❯

Citations

Jun 20, 2020·Organic & Biomolecular Chemistry·Lin-Yi XuXiang-Guo Hu

❮ 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.