The Construction of Anhydro Monosaccharides

Abstract

Anhydro monosaccharide is as pecific and distinctive category of carbohydrates, which is found in many naturally deriveda nd artificial bioactive substrates. In the field of organic chemistry,s ome anhydro sugars can be used as common synthons to construct different carbohydrate structures. The development of efficient methodologies for the constructiono fv ariousa nhydro sugar fragments is very important in carbohydrate chemistry,w hich has attracted considerable attention in the past few years. This reviewm ainly covers the development of new synthetic methods since 2000 and gives an overview of the development in the formation of anhydro monosaccharide structures. It systematically summarizes all methodst oe stablish an intramolecular ether bridge in furanose and pyranose structures, which are the mostc ommonly used monosaccharide fragments in carbohydrate chemistry.

Design, Synthesis and Biological Evaluation of Nitrate Derivatives of Sauropunol A and B as Potent Vasodilatory Agents

“…However, the detailed pharmaceutical investigation such as structure identification, organic synthesis and biological evaluation of single constituents of Sauropus rostratus was limited until a group of 2-deoxy-3,6-anhydro hexofuranoside derivatives 1 – 4 (Figure 1) were identified and isolated from leaves of Sauropus rostratus in 2014 [27]. Anhydro sugars constitute a specific and distinctive category of carbohydrates with intriguing physical, chemical and biological properties and thus, have attracted considerable attention from different chemical and pharmaceutical researchers, including our group [28,29,30]. Based on our recently developed synthetic strategy to construct 3,6-anhydro monosaccharides [31], the four naturally occurring 2-deoxy-3,6-anhydro hexofuranoside analogs 1 – 4 were synthesized and named by us [32].…”

Solvent‐Free Conversion of Alcohols to Alkyl Iodides and One‐Pot Elaborations Thereof

“…Success of the reaction is critically dependent on the generation of a 2,3‐ O ‐stannylene‐acetal as evidenced by the lack of cyclization observed in the absence of Bu 2 SnO (entry 8). This one‐pot strategy provided a convenient alternative both to strong alkali‐promoted cyclization and to previous examples of Bu 2 SnO mediated intramolecular etherification of tosylates,, requiring a stoichiometric amount of the toxic tin reagent, longer reaction times and high boiling solvents. Unlike tin–mediated intermolecular alkylations, no ammonium halide additive was needed for the cyclization.…”

“…On the other hand, many useful targets and building blocks can also be prepared through displacement of a leaving group at the primary position. Some important examples, that we selected in our investigation, are the installation of azides and sulfur‐containing functionalities, useful precursors in several synthetic applications, including the broadly applied click conjugations; further effort was also addressed towards the generation of exo ‐glycals and anhydrosugars representing relevant structures in organic and oligosaccharide synthesis.…”

Nucleophilic Ring‐Opening of 1,6‐Anhydrosugars: Recent Advances and Applications in Organic Synthesis

“…Since then, several natural products and therapeutically relevant carbohydrates involving the anomeric carbon in the anhydro motif to form a 6,8-dioxabicyclo[3.2.1]octane skeleton have been reported in the literature. [2] Examples include Coriariin, a tannin found in Coriaria japonica A [3] and ertugliflozin, an antidiabetic drug acting as a sodium/glucose cotransporter 2 (SGLT2) inhibitor. [4] Thanks to their intrinsic reactivity, 1,6-anhydrosugars offer numerous advantages as stable glycosylating agents having an unusual conformation ( 1 C 4 ).…”

“…[1] The word levoglucosan was indeed coined from “levo”, the compound is strongly levogyre, “gluco” for the glucose configuration and “an” for anhydro. Since then, several natural products and therapeutically relevant carbohydrates involving the anomeric carbon in the anhydro motif to form a 6,8‐dioxabicyclo[3.2.1]octane skeleton have been reported in the literature [2] …”