Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

Traverssi, Miqueas G.; Peñéñory, Alicia B.; Varela, Oscar; Colomer, Juan P.

doi:10.1039/d0ra09534f

Cited by 3 publications

(3 citation statements)

References 73 publications

(84 reference statements)

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“…Methyl 2,3,4,6-tetra- O -acetyl-1-deoxy-1-thio-β- d -glucopyranoside (2.389 g, 6.313 mmol, 1.0 equiv) was dissolved in anhydrous MeOH (20 mL). NaOMe in MeOH (25 wt %) was added in a dropwise fashion until pH 10 was reached.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…36 1 H NMR (400 MHz, CDCl 10.0 Hz, J 5,6a 3.9 Hz, J 5,6b 2.0 Hz, 1H, H5), 3.95−3.85 (m, 2H, H3, H4), 3.78 (dd, J 6a,6b 10.6 Hz, 1H, H6aa), 3.70−3.63 (m, 2H, H2, H6b), 2.07 (s, 3H, SCH 3 ). 13 37 (2.389 g, 6.313 mmol, 1.0 equiv) was dissolved in anhydrous MeOH (20 mL). NaOMe in MeOH (25 wt %) was added in a dropwise fashion until pH 10 was reached.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

et al. 2022

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The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.

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Section: Experimental Sectionmentioning

confidence: 99%