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Beilstein J. Org. Chem. 2018, 14, 856–860, doi:10.3762/bjoc.14.71
Graphical Abstract
Figure 1: Four possible isomers reachable through the presented approach.
Scheme 1: Sharpless epoxidation to gain D-galacto- 5a and L-galacto-configured epoxythreitol 5b.
Scheme 2: Reagents and conditions: a) i) (COCl)2, DMSO, Et3N, DCM, ii) triethyl phosphonoacetate, NaH, DCM; b...
Scheme 3: Proposed mechanism of the Pd-catalyzed azide substitution of 6a in protic solvent.
Scheme 4: Approach towards peracetylated D-IdoNAc 2c, reactions and conditions: a) Ti(OiPr)4, t-BuOOH, D-DET,...