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Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109
Graphical Abstract
Figure 1: Structure of squalenic acid-d6, gemcitabine and GemSQ-d6 conjugate.
Scheme 1: Retrosynthetic route to SQCO2H-d6 (1) and synthetic routes for the preparation of dialdehyde 5 and ...
Scheme 2: Implementation of the deuterated isopropylidene end-group by the Shapiro reaction of trisylhydrazon...
Scheme 3: Attempted synthesis of 1 via the protection of the aldehyde 10 as a 5,5-dimethyl-1,3-dioxane.
Scheme 4: Synthesis of squalenic acid-d6 1 and conjugation to gemcitabine.
Figure 2: A) Sketch depicting the procedure of preparing the NAs. B) Single Raman spectra of GemSQ-d6 NAs, Ge...