Protecting group-free method for synthesis of N-glycosyl carbamates and an assessment of the anomeric effect of nitrogen in the carbamate group

The quantitative pyrrole protection of l-phenylalanine/l-phenylalaninol in aqueous media and rationally updating the mechanisms of the Clauson-Kaas reaction through DFT study

“…The first protecting group-free synthesis of N -glycosyl carbamates has been realized by d -glucose with n -butyl carbamate being catalyzed in 2.4 M HCl/AcOEt. 17 The one-pot conversion of sustainable d -ribose with l -amino acid methyl esters produced pyrrole-2-carbaldehydes in reasonable yields under pressurized conditions with the assistance of oxalic acid in DMSO. 18 Although malonic acid was still adopted as the necessary catalyst, the amadori compound N -(1-deoxy- d -fructos-1-yl)- l -proline exhibits exemplarily much higher isomerization rates than d -fructose through the C-1 substituent-mediated intramolecular catalytic effect.…”

Structural, Electronic, Reactivity, and Conformational Features of 2,5,5-Trimethyl-1,3,2-diheterophosphinane-2-sulfide, and Its Derivatives: DFT, MEP, and NBO Calculations

“…This phenomenon is known as a "Generalized Anomeric Effect" (GAE) or "negative hyperconjugation" [12]. Experimental and theoretical approaches were used for the in-depth study of the AE [15,16]. Furthermore, depending on the relative amount of the distinct GAE eq.…”