117252-67-2

Upstream product

• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 

Downstream Products

• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 158923-94-5 2-(Trimethylsilyl)ethyl-<2,3,4-tri-O-benzyl-6-dimethylphenylsilyl-L-glycero-α-D-manno-heptopyranosid> 
• 158923-91-2 2-(Trimethylsilyl)ethyl-<2,3,4-tri-O-benzyl-6-0-methyl-α-D-mannopyranosid> 
• 158923-92-3 2-(Trimethylsilyl)ethyl-<2,3,4-tri-O-benzyl-α-D-mannopyranosid> 
• 158923-93-4 2-(Trimethylsilyl)ethyl-<2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranosid> 

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.