115969-51-2

Basic information

• Product Name: 2-(trimethylsilyl)ethyl lactoside
• Synonyms: 2-(trimethylsilyl)ethyl lactoside;2-(Trimethylsilyl)ethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
• CAS NO: 115969-51-2
• Molecular Formula: C₁₇H₃₄O₁₁Si
• Molecular Weight: 442.53076
• Mol File: 115969-51-2.mol

Chemical Properties

• Boiling Point: 642.6°Cat760mmHg
• Flash Point: 342.4°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 3.2E-19mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 2-(trimethylsilyl)ethyl lactoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trimethylsilyl)ethyl lactoside(115969-51-2)
• EPA Substance Registry System: 2-(trimethylsilyl)ethyl lactoside(115969-51-2)

Safety Data

• Hazardous Substances Data: 115969-51-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H34O11Si/c1-29(2,3)5-4-25-16-14(24)12(22)15(9(7-19)27-16)28-17-13(23)11(21)10(20)8(6-18)26-17/h8-24H,4-7H2,1-3H3/t8-,9-,10+,11+,12-,13-,14-,15-,16-,17+/m1/s1

Upstream product

• 14227-59-9 α-(2,3,4,6-tetra-O-acetyl-β-O-D-galactopyranosyl)-(1→4)-O-2,3,6-tri-O-acetyl-β-D-glucopyranosyl iodide 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 3616-19-1 lactose octaacetate 
• 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 

Downstream Products

• 117253-23-3 2-(trimethylsilyl)ethyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 115969-50-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 121377-27-3 2-(trimethylsilyl)ethyl O-(3-O-benzyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 
• 128716-18-7 2-(trimethylsilyl)ethyl O-<3-O-(4-methoxybenzyl)-β-D-galactopyranosyl>-(1->4)-β-D-glucopyranoside 
• 160533-98-2 2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 117253-41-5 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 117253-25-5 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 164525-86-4 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside 
• 160533-61-9 2-(trimethylsilyl)ethyl 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 160533-73-3 4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-β-D-galactopyranosyl>-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate 
• 160534-00-9 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-O-<2,3-di-O-benzoyl-6-O-p-methoxybenzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxo-hexopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 
• 160533-96-0 2-(trimethylsilyl)ethyl (2,3-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and biological evaluation of a new sialyl Lewis X mimetic derived from lactose

A sialyl Lewis X (sLex) mimetic compound, 2-(trimethylsilyl)ethyl 3-O-carboxymethyl-β-D-galactopyranosyl-(1→4)-[α-L-fucosyl- (1→6)]-β-D-glucopyranoside (2a), has been synthesized in 14 steps from D-lactose. This synthesis features the use of the activated glycosylating donor, lactosyl iodide, in a Koenigs-Knorr sequence, the regioselective derivatization at the C-3 position of the galactose moiety, and the stereoselective construction of a fucose-α(1→6)-lactose linkage. The mimetic was tested for its ability to inhibit human polymorphonuclear leukocyte (hPMNL) adhesion to immobilized recombinant human E-selectin under shear stress conditions.

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.