Synthesis of 3-deoxy-3,3-difluoro-d-ribohexose from gem-difluorohomoallyl alcohol

Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose and assessment of their erythrocyte transmembrane transport

“…Treatment of 13 with Deoxofluor TM generated the trifluoroacetal 15. Selective deprotection of the benzyl ether was accomplished by the method of Adinolfi et al 13 to give 16 and then Dess-Martin oxidation gave the unstable a-fluoroaldehyde 17 which was immediately subjected to acetonide cleavage and intramolecular cyclisation, using SnCl 2 in CH 2 Cl 2 14 to generate the D-glucose analogue 9. The free sugar 9 is a white crystalline solid and a suitable crystal was subjected to X-ray structure analysis to confirm the relative and absolute stereochemistry which was consistent with configurational inversions for each C-F bond forming reaction.…”

Quantitative Analysis of 2D EXSY NMR Spectra of Strongly Coupled Spin Systems in Transmembrane Exchange

“…The tetrafluorinated sugar derivative 6 was obtained using a synthetic route developed in our laboratory [29] . The difluorinated glucose analogue 7 was produced by adapting established methods [30,37] . Stock solutions of fluorosugars were prepared in deuterated saline that consisted of 154 mM NaCl in 99 % D 2 O sourced from the Australian Institute of Nuclear Science and Engineering (Lucas Heights, NSW, Australia).…”

“…[27] Following the earlier work on RBC membrane transport of hexafluorinated 5 [23] and 2,3,4-trideoxy-2,3,4-trifluorinated glucose, [28] we had set out to investigate membrane transport of glucose substrates with different fluorination patterns using EXSY NMR; the compounds included 2,3-dideoxy-2,2,3,3-tetra-fluorinated glucose (6, Figure 2; FDG2233) [29] and 3-deoxy-3,3difluorinated analogue 7 (FDG33). [30] We found that the established back-transformation analysis methodology for 19 F 2D EXSY quantification (cross-peak identification, integration, and kinetic model fitting) of polyfluorinated substrates was no longer tractable due to additional quantum mechanical spin processes (listed in the Introduction) that do not exist in monofluorinated substrates. To overcome this obstacle, we used numerical least squares fitting of the two-dimensional experimental spectra using Spinach software that explicitly models all aspects of coherent, dissipative, and chemical spin dynamics, including a pulse-by-pulse implementation of the 2D EXSY sequence in the time domain.…”

“…Following the earlier work on RBC membrane transport of hexafluorinated 5 [23] and 2,3,4‐trideoxy‐2,3,4‐trifluorinated glucose, [28] we had set out to investigate membrane transport of glucose substrates with different fluorination patterns using EXSY NMR; the compounds included 2,3‐dideoxy‐2,2,3,3‐tetrafluorinated glucose ( 6 , Figure 2 ; FDG2233) [29] and 3‐deoxy‐3,3‐difluorinated analogue 7 (FDG33). [30] …”

Research on Synthesis of Hexafluoropropylene

“…HFPO is an important perfluorinated oxygen compound; it has become the intermediate product of many important organic fluorine materials of functionality because of the unique chemical activity of its three-ring structure [1,6]. It has a wide application in the synthesis of PSVE, fluorinated polyether, FS, HFA and so on.…”