N‐Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

Abstract

While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides.

Synthesis and glycosidation of building blocks of D-altrosamine

“…Early reports for the synthesis of rare sugar D-altrose relied on the degradation of heptuloses ( Ritchmyer et al, 1939 ) or modification of fructose ( Araujo et al, 2012 ) among others. The synthesis of D-altrosamine could be achieved from 2,3-anhydroaltrose that was obtained from D-glucose precursors via a multi-step protocol ( Vega-Perez et al, 1995 ; Nilsson and Norberg, 2000 ; Chiu et al, 2007 ; Shrestha et al, 2022 ). These building blocks have previously been used as synthons to access derivatized rare sugars.…”