162222-93-7

Basic information

• Product Name: (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol
• Synonyms: (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol
• CAS NO: 162222-93-7
• Molecular Weight: 532.677
• Mol File: 162222-93-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol(162222-93-7)
• EPA Substance Registry System: (1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol(162222-93-7)

Safety Data

• Hazardous Substances Data: 162222-93-7(Hazardous Substances Data)

Upstream product

• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 107802-80-2 (2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran 
• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 

Downstream Products

• 187402-14-8 (1R,2R)-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cyclohexyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 
• 172494-09-6 (1R,2R)-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-cyclohexyl 6-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

Synthesis of sialyl Lewis(x) mimics: Replacement of galactose by aromatic spacers

Six sLe(x) mimics where the galactose moiety is replaced by aromatic spacers have been prepared and tested for their binding affinity to E-selectin.

Design and synthesis of E-selectin antagonists

Selectin-mediated recruitment of leukocytes plays a crucial role in a number of diseases and pathological situations, for example in inflammation, reperfusion injury, rheumatoid arthritis and respiratory diseases. Substantial research efforts are directed toward development of carbohydrate-derived drugs that interfere with the inflammatory response by blocking the selectin binding site. This article describes two approaches for the improvement of the inhibitory potency of the lead structure sialyl Lewisx (sLex). One approach is based on the preorganization of mimics in their bioactive conformation to reduce entropic costs. For the conformational analysis of mimics, molecular modeling based tools were developed. They allow the rational design of selectin antagonists with simplified structures, but increased inhibitory potency. Alternatively, additional carbohydrate/lectin contacts can be identified for the improvement of enthalpic contributions. Following this approach, an additional hydrophobic interaction of the antagonists with E-selectin leads to a 60-fold improvement of E-selectin affinity. Antagonists have been synthesized using chemical or chemo-enzymatic methods. Finally, a flow chart for the biological evaluation of the antagonists is presented.

Synthesis of novel mimetics of the sialyl Lewis X determinant

Mimetics of the sialyl Lewis-X determinant in which at least one sugar domain is simulated by a di-, tri- or tetraalcohol unit have been synthesized. The inhibitory potency of these compounds for E- and P-selectin mediated cell adhesion has been evaluated in cell culture assays. The receptor binding affinity of the best of these mimetics was slightly higher than that of the natural oligosaccharide ligand sialyl Lewis X.