154092-32-7

Upstream product

• 14262-87-4 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 166241-68-5 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 127305-34-4 2,3,4,6-tetra-O-Bz-α-D-mannopyranosyl bromide 

Relevant academic research and scientific papers

A catalytic Koenigs-Knorr glycosylation based on acceptor activation with In(NTf2)3

The development of efficient glycosylation methods is important for gaining better insight into biological processes of significance to medicinal chemistry. Herein, we describe an In(NTf2)3 -catalyzed Koenigs-Knorr glycosylation based on the activation of an alcoholic hydroxyl group. A catalytic amount of In(NTf2)3 enables effective glycosylation of diverse alcohols with peracylated aldosyl bromides as donors, leading to the stereoselective formation of a series of glycosides in satisfactory yields. The protocol is characterized by mild reaction conditions and good functional-group tolerance, while obviating any need for any additive. Moreover, the potential utility of this transformation is demonstrated by the convenient syntheses of key building blocks for biomolecules of medicinal relevance.

Synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranosides revisited

Glycosylation of 2-(trimethylsilyl)ethanol with various ethyl 1-thioglycosides, which were activated with N-iodosuccinimide and silver triflate, was studied. The starting thioglycosides, some prepared for the first time, were obtained conventionally from the corresponding α-1-acetates. When β-1-acetates were more readily available, these were converted to the α-anomers by anomerization, prior to the glycosylation. Using ethyl 1-thioglycosides as glycosyl donors, especially those bearing a pivaloyl or a nonparticipating group at O-2, the corresponding 2-(trimethylsilyl)ethyl α-D-mannopyranosides were obtained in excellent yields.

A synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranoside

The first high yield synthesis is reported of 2-(trimethylsilyl)ethyl α-D-mannopyranoside using 2-O-benzoylated mannosyl donors, as precursors.