252896-26-7

Basic information

• Product Name: 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester
• Synonyms: 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester
• CAS NO: 252896-26-7
• Molecular Weight: 1061.28
• Mol File: 252896-26-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester(252896-26-7)
• EPA Substance Registry System: 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester(252896-26-7)

Safety Data

• Hazardous Substances Data: 252896-26-7(Hazardous Substances Data)

Upstream product

• 187404-16-6 benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate 
• 252896-25-6 (2R,3R,4S,5R,6R)-2-[(2R,3S,4R)-2-Benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 252896-24-5 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R)-2-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester 
• 161313-45-7 (2R)-2-hydroxy-3-cyclohexyl-propionic acid benzyl ester 
• 156469-00-0 (2R)-3-cyclohexyl-2-hydroxypropionic acid 
• 76946-04-8 perbenzyl fucosyl bromide 
• 131545-02-3 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 828-01-3 D-phenyllactic acid 
• 135214-83-4 1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside 
• 252896-22-3 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,4aR,8R,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-4-yl ester 
• 252896-23-4 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Synthesis and Biological Evaluation of a Potent E-Selectin Antagonist

An early step of the inflammatory response - the rolling of leukocytes on activated endothelial cells - is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialyl Lewisx (sLex) 1 is a ligand for E-, P-, and L-selectin and, therefore, serves as a lead structure to develop analogues which allow the control of acute and chronic inflammation. Here we describe the efficient synthesis (10 linear steps) of the potent sLex mimetic 2. Compared to sLex, compound 2 showed a 30-fold improved affinity in a static, cell-free E-selectin-ligand binding assay (IC50 = 36 μM). These data were confirmed by a marked inhibition in an in vitro cell-cell rolling assay which simulates in vivo conditions (IC50 ca. 40 μM). The assays are predictive for the in vivo efficacy of test compounds as indicated by a marked inhibitory effect of 2 in a thioglycollate induced peritonitis model of acute inflammation in mice (ED50 ca. 15 mg/kg).