33208-48-9Relevant articles and documents
Synthesis of protected glucose derivatives from levoglucosan by development of common carbohydrate protecting group reactions under continuous flow conditions
Marion, Keevan C.,Wooke, Zachary,Pohl, Nicola L.B.
, p. 23 - 29 (2018)
Common carbohydrate protecting group reactions under continuous flow processes are reported in the context of producing partially-protected glucose building blocks from levoglucosan. Benzyl ether protection was demonstrated without the use of NaH using ba
Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
supporting information, p. 13499 - 13506 (2020/10/02)
In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.
PROSTANOIDS. LVI. USEFUL PROSTAGLANDIN SYNTHONS FROM LEVOGLUCOSAN
Tolstikov, G. A.,Valeev, F. A.,Ibragimova, I. P.,Gaisina, I. N.,Spirikhin, L. V.,Miftakhov, M. S.
, p. 1501 - 1506 (2007/10/02)
(1S,6S,7R,9R)-7,9-Dihydroxy-3-oxabicyclononan-4-one, which is a new chiral synthon for cyclopentanoids, was obtained by intramolecular radical cyclization of methyl 4R,6S-dibenzyloxy-7R-hydroxy-8-acetoxyoct-2E,Z-enoates and subsequent removal of th
