173347-84-7Relevant academic research and scientific papers
Polycyclic trans-Fused Crown Ethers From D-Mannitol
Nazhaoui, Mostafa,Gross, Bernard,Joly, Jean-Pierre
, p. 1287 - 1290 (1993)
New macrocyclic ethers, all bearing a common trans-fused chiral dioxepan moiety, were easily synthesized from 1,3:4,6-di-O-benzylidene-D-mannitol in 5 or 6 steps (3 examples).The influence of the substituent at C-1/C-6 position upon conformation is discus
trans-Fused crown ethers from 2,5-O-methylene-D-mannitol: synthesis, X-ray diffraction structure and full nuclear magnetic resonance spectroscopic data of 1,6-diazido-1,6-dideoxy-2,5-O-methylene-3,4-O-naphthalene-2,3-diylbis(oxyethyleneoxyethylene)-D-mannitol and 3,4-di-O-acetyl-1,6-...
Nazhaoui, Mostafa,Joly, Jean-Pierre A.,Jean-Claude, Bertrand J.,Duca, Valerio Del,Aubry, Andre,Boubouh, Mohammed
, p. 2919 - 2926 (2007/10/02)
The crystalline compound 5, named in the title and prepared from technical D-mannitol in 6 steps, has been fully investigated by different spectroscopic methods including MS, IR, 1H, 13C, 14N and 15N NMR.These results confirm the perfect C2-cymmetry in solution and provide the complete map of this chiral homotopic crown ether.X-ray diffraction analysis of compound 5 reveals it exists in a distorted chair conformation as one monocyclic precursor 14.Treatment of compound 5 with acetylene derivatives gave the macrocycles 6 and 7 with bulky symmetric triazole substituents.The anomalous lack of complexing abilities of compounds 5, 6, and most related macrocycles towards phenylglycine methyl ester perchlorates could be explained by the rigidity of the dioxepane framework around the C-3/C-4 axis of D-mannitol.
