Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate-Nitroalkane Medium and Diversification at the 4'-Nitrogen Position.

Title Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate-Nitroalkane Medium and Diversification at the 4'-Nitrogen Position.
Authors T. Shoji; S. Kim; K. Chiba
Journal Angew Chem Int Ed Engl
DOI 10.1002/anie.201700547
Abstract

Azanucleosides, in which the 4'-oxygen atom has been replaced with a nitrogen atom, have drawn much attention owing to their anticancer and antivirus activity, and tolerance towards nucleases. However, the traditional synthetic strategy requires multiple steps and harsh conditions, thereby limiting the structural and functional diversity of the products. Herein we describe the synthesis of azanucleosides by an electrochemical reaction in a lithium perchlorate-nitroethane medium, followed by postmodification at the 4'-N position. N-Acryloyl prolinol derivatives were converted into azanucleosides by anodic activation of the N-?-C-H bond. Moreover, the use of nitroethane instead of nitromethane lowered the oxidation potential of the N-acryloyl prolinols and increased the Faradic yield. The prepared azanucleosides were efficiently functionalized at the 4'-N-acryloyl group with a lipophilic alkanethiol and a fluorescent dye by conjugate addition and olefin cross-metathesis, respectively.

Citation T. Shoji; S. Kim; K. Chiba.Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate-Nitroalkane Medium and Diversification at the 4'-Nitrogen Position.. Angew Chem Int Ed Engl. 2017;56(14):40114014. doi:10.1002/anie.201700547

Related Elements

Lithium

Lithium Bohr ModelSee more Lithium products. Lithium (atomic symbol: Li, atomic number: 3) is a Block S, Group 1, Period 2 element with an atomic weight of 6.94. The number of electrons in each of Lithium's shells is [2, 1] and its electron configuration is [He] 2s1. The lithium atom has a radius of 152 pm and a Van der Waals radius of 181 pm. Lithium was discovered by Johann Arvedson in 1817 and first isolated by William Thomas Brande in 1821. The origin of the name Lithium comes from the Greek wordlithose which means "stone." Lithium is a member of the alkali group of metals. It has the highest specific heat and electrochemical potential of any element on the period table and the lowest density of any elements that are solid at room temperature. Elemental LithiumCompared to other metals, it has one of the lowest boiling points. In its elemental form, lithium is soft enough to cut with a knife its silvery white appearance quickly darkens when exposed to air. Because of its high reactivity, elemental lithium does not occur in nature. Lithium is the key component of lithium-ion battery technology, which is becoming increasingly more prevalent in electronics.

Related Forms & Applications