117253-49-3

Upstream product

• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 108-24-7 acetic anhydride 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 117253-14-2 2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside 
• 103082-76-4 2'-trimethylsilylethanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 117252-95-6 2-(trimethylsilyl)ethyl β-D-galactopyranoside 
• 117253-16-4 2-(trimethylsilyl)ethyl 2-O-benzyl-β-D-galactopyranoside 
• 117253-15-3 2-(trimethylsilyl)ethyl 2-O-benzyl-3,4-O-isopropylidene-6-O-(2-methoxyisopropyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Indium(III) triflate: A highly efficient catalyst for reactions of sugars

Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.

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.