1055034-25-7

Upstream product

• 100-39-0 benzyl bromide 
• 112-53-8 1-dodecyl alcohol 
• 604-69-3 β-D-glucose pentaacetate 
• 59122-55-3 n-dodecyl-b-D-glucopyranoside 
• 258349-79-0 n-dodecyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 258349-80-3 n-dodecyl 4,6-O-benzylidene-2,3-di-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 1309439-38-0 n-dodecyl 2,3-O-dibenzyl-4,6-O-[16-crown-5]-β-D-glucopyranoside 
• 1309439-36-8 n-dodecyl 2,3-O-dibenzyl-4,6-O-[19-crown-6]-β-D-glucopyranoside 
• 1309439-34-6 n-dodecyl 2,3-di-O-dibenzyl-4,6-bis-O-[2-hydroxyethyl]-β-D-glucopyranoside 
• 1309439-35-7 C₄₄H₆₈O₁₀ 

Relevant academic research and scientific papers

Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition

A series of new mix aza- and thia-macrocyclic glycolipids (9, 10, 16 and 17) have been synthesized and their enantiomeric selectivity was studied. The synthesis of the macrocycles involved a simple protection of two hydroxyl groups of the glycolipids followed by building up the mix-heteroatom macrocyclic in simple sequences. The macrocycles and previously investigated analogues (18, 19, 20 and 21) have been applied as phase transfer catalysts in the enantioselective Michael addition of 2-nitropropane to chalcone and showed good-to-excellent enantiomer excess (ee). Among the catalysts, the galactose aza-crown ether-based glycolipid 21 proved to be the most effective with 90% ee. Graphic abstract: [Figure not available: see fulltext.]

Interactions of hydroxy compounds and sugars with anions

Complexations of aliphatic monohydroxy compounds, of trans-1,2 cyclohexanediol, and of several glucose and galactose derivatives with two to four free hydroxy groups are measured in chloroform with peralkylammonium salts containing different anions. It is shown that NMR titrations with up to four different OH signals as well as with some CH signals allow accurate and consistent calculation of equilibrium constants K and complexation induced shifts (CIS). The anions used generally show an increasing affinity in the order iodide 3 M-1 for 1-dodecyl glucose or galactose compounds. The observed CIS and K values agree with the formation of 3 different 1:1 complexes of similar stability for the phosphate receptor, with binding one anion between the 2-, 3-, 4-, and 6-OH groups of the glucoside, or only one 1:1 complex in the interaction of halides with sugars. Vicinal 3JHOCH coupling constants are analyzed before and after complexation and provide insight into the hydrogen bond network of the sugar derivatives.