154092-35-0

Upstream product

• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 98-88-4 benzoyl chloride 
• 515813-83-9 1,3,4,6-tetra-O-acetyl-2-O-benzoyl-β-D-mannopyranose 

Downstream Products

• 154092-38-3 Benzoic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-chloro-tetrahydro-pyran-3-yl ester 
• 515813-86-2 ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside 
• 154092-41-8 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-α-D-mannopyranoside 
• 154092-46-3 Acetic acid (3aS,5R,6R,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-phenyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester 

Relevant academic research and scientific papers

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.