143571-58-8

Basic information

• Product Name: 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
• Synonyms: 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
• CAS NO: 143571-58-8
• Molecular Weight: 550.767
• Mol File: 143571-58-8.mol

Chemical Properties

• CAS DataBase Reference: 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside(143571-58-8)
• EPA Substance Registry System: 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside(143571-58-8)

Safety Data

• Hazardous Substances Data: 143571-58-8(Hazardous Substances Data)

Upstream product

• 128200-64-6 2-(trimethylsilyl)ethyl 3-O-allyl-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 143834-54-2 2-(trimethylsilyl)ethyl 3-O-p-methoxybenzyl-β-D-galactopyranoside 
• 117252-95-6 2-(trimethylsilyl)ethyl β-D-galactopyranoside 
• 143834-55-3 {2-[(2R,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-trimethyl-silane 
• 128200-65-7 2-(trimethylsilyl)ethyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside 

Downstream Products

• 143571-59-9 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 438216-07-0 [(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-(dimethoxy-phosphoryl)-acetic acid methyl ester 
• 143571-62-4 C₇₄H₈₇NO₁₅Si 
• 143571-63-5 2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 143571-61-3 N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide 
• 143571-60-2 2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 509085-99-8 Diazo-acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester 
• 197243-30-4 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate 
• 197243-29-1 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-β-D-galactopyranoside 
• 197243-27-9 [(2R,3R,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester 
• 197243-26-8 (2R,3S,5S,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-one 
• 181718-68-3 (2S,3S,4S,5R,6R)-3-Acetoxy-5-benzoyloxy-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Catalytic conversions of diazosugars

Catalytic diazo decomposition chemistry was explored with novel diazoacetate functionalized carbohydrates. In both glucose and galactose derivatives, aromatic cycloadditions with the benzyl protecting groups proved to be most favorable reactions. Replacing the benzyl groups by methoxy groups in the glucose system led to formation of 'carbene dimers'.

A simple method for the removal of 4-methoxybenzyl group

Removal of 4-methoxybenzyl group from a series of compounds having various protecting groups has been achieved by treatment with 80% acetic acid in water at 80°C for 4 hours.

Synthesis of the globotetraose tetrasaccharide and terminal tri- and di-saccharide fragments

The 2-(trimethylsilyl)ethyl (TMSEt) β-glycosides of globotetraose 3)-α-D-Gal-(1 -> 4)-β-D-Gal-(1 -> 4)-D-Glc> and the terminal trisaccharide, as well as the methyl α-glycoside 1 of the terminal disaccharide, were synthesised by silver trifluoromethanesulfonate-promoted β-glycosylation of suitably protected galactoside, galabioside, and globotrioside alcohols with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl chloride, followed by removal of protecting groups.Removal of the anomeric TMSEt group of the globotetraoside and of the terminal trisaccharide, using trifluoroacetic acid-dichloromethane, gave the corresponding hemiacetal sugars 8 and 3.The TMSEt glycoside of the terminal trisaccharide was converted, via the 1-acetate, into the corresponding isobutyl (4) and 3-butylsulfonyl-2-propyl (5) glycosides and into the TMSEt thioglycoside 6 via the glycosyl bromide.