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60431-34-7, 2,3,4-Tri-O-benzyl-L-fucopyranose , CAS:60431-34-7

60431-34-7, 2,3,4-Tri-O-benzyl-L-fucopyranose ,
CAS:60431-34-7
C27H30O5 / 434.52
MFCD00153596

2,3,4-Tri-O-benzyl-L-fucopyranose

2,3,4-三-O-苄基-L-吡喃岩藻糖,

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 Number60431-34-7
Product Name2,3,4-Tri-O-benzyl-L-fucopyranose
IUPAC Name(3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
Molecular FormulaC27H30O5
Molecular Weight434.52 g/mol
InChIInChI=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 KeyYRAQXZMHYZXWBZ-OGPNLZSQSA-N
SMILESCC1C(C(C(C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Synonyms6-Deoxy-2,3,4-tri-O-(phenylmethyl)-L-galactose
Canonical SMILESCC1C(C(C(C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
Isomeric SMILESC[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.: C27H30O        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


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