117253-41-5

Upstream product

• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 103082-77-5 2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 115969-51-2 2-(trimethylsilyl)ethyl O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 100-39-0 benzyl bromide 
• 77-76-9 2,2-dimethoxy-propane 
• 117253-40-4 2-(trimethylsilyl)ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 117253-42-6 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

A practical method for the synthesis of sialyl α-glycosides

Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0°C affords the sialic acid donor α-2-(methylthio)-3-thiosialic

2-(Trimethylsilyl)ethyl Glycosides. Synthesis, Anomeric Deblocking, and Transformation into 1,2-Trans 1-O-Acyl Sugars

Twenty-seven mono --> tetrasaccharidic 2-(trimethylsilyl)ethyl (TMSET) glycosides were synthesized by the Koenigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry.Variously protected TMSET glycosides were treated with BF3*Et2O (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55 deg C, which gave in one step the corresponding protected 1-O-acyl sugars.In the majority of cases, the yields of purified compounds exceeded 90percent and the anomeric configuration of the starting TMSET glyoside was conserved to a large extent (>95percent) in most of the 1-O-acylated products.Unprotected and acetyl-, benzoyl-, benzyl-, dimethyl-tert-butylsilyl-, and phthaloyl-protected mono-->tetrasaccharidic TMSET glycosides were anomerically deblocked by using trifluoroacetic acid in dichloromethane at 0-22 deg C for 10-30 min.The hemiacetal products were isolated in 88-96percent yield; all reagents and byproducts were volatile and easily removed.