Stereoselective Synthesis of D-5-Homo-4-selenoribose as a Versatile Intermediate for 4'-Selenonucleosides

Organic Letters
Gyudong KimLak Shin Jeong

Abstract

Stereoselective synthesis of D-5-homo-4-selenoribose, serving as a versatile intermediate for the synthesis of 4'-selenonucleosides 12a-c, was accomplished using Sharpless asymmetric epoxidation, regioselective cleavage of the α,β-epoxide, and stereoselective reduction of the ketone as the key steps.

References

Nov 5, 2005·The Journal of Organic Chemistry·Francisco Sarabia, Antonio Sánchez-Ruiz
Jan 16, 2007·Carbohydrate Research·John K GallosAlexandros E Koumbis
Nov 22, 2007·Nucleic Acids Symposium Series·Yusuke InagakiAkira Matsuda
Dec 20, 2007·Organic Letters·Lak Shin JeongLong Xuan Zhao
Mar 5, 2008·Carbohydrate Research·Kumarasamy JayakanthanB Mario Pinto
Jun 12, 2008·Journal of the American Chemical Society·Jonathan K WattsMasad J Damha
Sep 9, 2008·Nucleic Acids Symposium Series·Yusuke InagakiAkira Matsuda
Nov 4, 2008·Bioorganic & Medicinal Chemistry·Lak Shin JeongJungwon Choi
Feb 23, 2012·Organic & Biomolecular Chemistry·Krishnammagari Suresh Kumar, Cirandur Suresh Reddy
Jun 1, 2013·Nature Reviews. Drug Discovery·Lars Petter JordheimCharles Dumontet

❮ Previous
Next ❯

Citations

Jun 20, 2017·Current Protocols in Nucleic Acid Chemistry·Pramod K SahuLak Shin Jeong
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Yuichi YoshimuraNoriaki Minakawa
Jul 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gabriella Vitali ForconesiRenata Riva

❮ 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.

Related Papers

Journal of Peptide Science : an Official Publication of the European Peptide Society
Wei ZhangYingxia Li
© 2021 Meta ULC. All rights reserved