74774-20-2Relevant academic research and scientific papers
Functionalised Carbocycles from Carbohydrates. Part 2. The Synthesis of 3-Oxa-2-azabicyclooctanes. X-Ray Crystal Structure of (1R,5S)-6-exo,7-endo,8-exo-Triacetoxy-N-methyl-4-endo-phenylthio-3-oxa-2-azabicyclooctane
Ferrier, Robert J.,Furneaux, Richard H.,Prasit, Petpiboon,Tyler, Peter C.,Brown, Kevin L.,at al.
, p. 1621 - 1628 (2007/10/02)
Treatment of various 6-bromo-6-deoxy- and 6-deoxy-6-iodo-D-glucopyranosyl compounds with zinc in ethanol affords acyclic 5,6-dideoxy-D-xylo-hex-5-enoses which have been converted into 3-oxa-2-azabicyclooctanes containing functional groups which per
Photobromination of Carbohydrate Derivatives. VI. Funcionalization at C6 of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose
Ferrier, Robert J.,Furneaux, Richard H.
, p. 1025 - 1036 (2007/10/02)
Photobromination of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose gives the syrupy 6S (exo) bromide in high yield; further reaction leads to secondary bromination at this position.The monobromide reacts with methanol and thiophenol under conditions of kinetic control to give mainly the endo-methoxy and phenylthio derivatives formed by direct nucleophilic displacement, and from the latter the exo-methoxy acetal was obtained by a second nucleophilic substitution.Acetolysis of these compounds can lead to the coresponding exo-6-acetoxy ester or monocyclicproducts formed by opening of the five-membered rings.
