2,3,4-Tri-O-benzyl-L-fucopyranose is a synthetic compound that activates the selectin receptor on the surface of white blood cells. It has been shown to activate the cell surface receptors for the lectin mannose and mannose-binding protein which are involved in the recognition of pathogens. 2,3,4-Tri-O-benzyl-L-fucopyranose is also able to inhibit magnesium ion binding to its target site on the bacterial surface. This inhibition prevents bacteria from attaching themselves to host tissues or other cells by binding with these sites. The compound was synthesized by a stereoselective method using silver trifluoromethanesulfonate as an activating reagent and can be used as an antimicrobial agent in mammals.
| CAS Number | 60431-34-7 |
| Product Name | 2,3,4-Tri-O-benzyl-L-fucopyranose |
| IUPAC Name | (3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol |
| Molecular Formula | C27H30O5 |
| Molecular Weight | 434.52 g/mol |
| InChI | InChI=1S/C27H30O5/c1-20-24(29-17-21-11-5-2-6-12-21)25(30-18-22-13-7-3-8-14-22)26(27(28)32-20)31-19-23-15-9-4-10-16-23/h2-16,20,24-28H,17-19H2,1H3/t20-,24+,25+,26-,27?/m0/s1 |
| InChI Key | YRAQXZMHYZXWBZ-OGPNLZSQSA-N |
| SMILES | CC1C(C(C(C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4 |
| Synonyms | 6-Deoxy-2,3,4-tri-O-(phenylmethyl)-L-galactose |
| Canonical SMILES | CC1C(C(C(C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4 |
| Isomeric SMILES | C[C@H]1[C@H]([C@H]([C@@H](C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4 |
| CAS No: 60431-34-7 MDL No: MFCD00153596 Chemical Formula: C27H30O5 Molecular Weight: 434.52 |
COA:
Product name: 2,3,4-Tri-O-benzyl-L-fucopyranose CAS: 60431-34-7
M.F.: C27H30O5 M.W.: 434.52 Batch No: 20130411 Quantity: 124g
|
Items |
Standards |
Results |
|
Appearance |
White to off-white solid |
Complies |
|
Solubility |
Easily soluble in CH2Cl2 |
Complies |
|
MS and NMR |
Should comply |
Comply |
|
Water |
Max. 0.5% |
0 |
|
Solvent Content (by GC) |
Max. 2% |
0.01% |
|
TLC |
One spot |
One spot |
|
Assay (alpha and beta) |
Min. 95% |
98.3% |
References:
1. Sakagami M, Horie K, Higashi K, Yamada H, Hamana H, Chem. Pharm. Bull. 1999, 47, p1237
| Size | 1 G, 100 MG, 5 G, Other |
|---|
10 in stock
10 in stock
10 in stock
10 in stock
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