Ram, Ram N.; Kumar, Neeraj; Kumar Gupta, Dharmendra published the artcile< Substrate-Controlled Diastereoselective Synthesis of Sugar-Based Chlorinated Perhydrofuro[2,3-b]pyrans via Copper(I)-Catalyzed Radical Cyclization>, Synthetic Route of 4098-06-0, the main research area is Ferrier rearrangement chloroethanol acetal glucal cyclization glycoside disaccharide preparation; crystal structure disaccharide stereoselective cyclization copper catalyzed hydrofuropyran chlorinated.
The work describes the first copper(I) chloride/2,2′-bipyridine-catalyzed atom transfer radical cyclization (ATRC) of unsaturated carbohydrate-derived chloroacetals to generate chlorinated perhydrofuro[2,3-b]pyrans via an effective diastereoselective route. Various glycals (glucal, galactal and lactal) underwent the Ferrier rearrangement with 2,2,2-trichloroethanols to give acetal precursors stereoselectively, R-selective with galactal in contrast to S-selective with glucal. The radical cyclization of the Ferrier products occurred smoothly to afford cis-fused bicyclic products with the transfer of the chlorine atom at the non-anomeric carbon in the cyclized radical intermediate predominantly from the equatorial direction. The carbohydrate templates controlled the stereochem. of both Ferrier rearrangement and ATRC steps. The stereo-structures of the products were also supported by single crystal X-ray diffraction crystallog. The products possess biol. important structural segments such as a glycosidic linkage, a fused bicyclic acetal unit and a chlorosugar unit which are potential sources for biol. studies and further synthetic elaborations.
Advanced Synthesis & Catalysis published new progress about Bicyclic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Synthetic Route of 4098-06-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics