Development of the methodology for the synthesis of bis-aminoinositols

Download

index.pdf

Date

2011

Author

Çokol, Nalan Korkmaz

Metadata

Show full item record

Item Usage Stats

173
views

64
downloads

Cyclitols are cyclic compounds having hydroxyl groups which attached to different carbons on the ring. Cyclitols have attracted a great deal of attention for having diverse biological activities. Cyclic alcohols play an important role in biological processes such as inhibition of glycosidase, cellular recognition, and signal transduction. In addition to this, these compounds are very important molecules due to being capable of using while synthesizing natural products or pharmaceuticals. In this study, development of new methodology for the synthesis of bis-aminoinositol derivatives was aimed. The starting material, cis-diester, was synthesized from the Diels-Alder reaction of furan and maleic anhydride followed by reaction with MeOH. As a second key compound, trans-diester was obtained from the Diels-Alder reaction of furan and fumaryl chloride followed by esterification. The diester functionality in these two compounds was planned to be converted into the hydrazide upon treatment with hydrazine monohydrate. Before this reaction, double bond was protected via stereo selective oxidation reaction with m-CPBA due to preventing retro Diels-Alder reaction. Then, hydrazide functionality was converted into acyl azide through β-nitroso hydrazide intermediate. Subsequent Curtius rearrangement reaction resulted in the formation of the isocyanate which was converted to the corresponding bis-urethane by treatment with MeOH. Attempt to cleave the oxa-bridge in urethane with sulfamic acid provided the unexpected tricyclic product 148. Furthermore, hydrolysis of isocyanate with aqueous HCl formed the diamine 156. However, O-bridge could not be opened with any reagents used for that of urethane derivative as described above. Then,the cis-diol 157 was synthesized to prevent the neighboring group participitation during the epoxide-opening reaction. Further ring-opening reactions are under investigation.

Subject Keywords

Cyclitols

URI

http://etd.lib.metu.edu.tr/upload/12613580/index.pdf
https://hdl.handle.net/11511/21081

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Development of new synthetic methodologies for aminocyclitols Ekmekçi, Zeynep; Balcı, Metin; Department of Chemistry (2011) Aminocyclitols are cyclitols in which at least one of the hydroxyl groups is exchanged with an amino functional group. In turn, they constitute a wide group of natural products with interesting biological properties and are widely distributed throughout. In particular, antibiotics containing an aminocyclitol unit have stimulated the development of synthetic methodologies in the search for analogues with enhanced pharmacological profiles. In this study, three different methods were applied to synthesize diam...
A theoretical study on the strong codimer of C-60 and Si-60, C58Si58 Türker, Burhan Lemi (2001-07-09) The strong codimer Of C-60 and Si-60 that is C58Si58 is considered for AM1 type semiempirical molecular orbital treatment at the, restricted Hartree-Fock level. The results reveal that C58Si58 structure should be highly endothermic but a stable molecule. The structure is expected to have some nonlinear properties.
Design of functional materials using liquid crystals as molecular templates Karausta, Aslı; Büküşoğlu, Emre; Kalıpçılar, Halil; Department of Chemical Engineering (2018) Liquid crystal (LC) is a phase of material which is intermediate to a crystalline solid and an isotropic liquid such that the molecules flow but retain a degree of long-range orientational ordering. LCs, due to their long range orientational ordering and fluidic properties, can be used in templated synthesis of polymeric materials as well as self assembly of the microparticles incorporated into the LCs. In the first part of this thesis, we sought to provide control over alignment of the polymer chains, alig...
Development of a novel PANI@WO3 hybrid composite and its application as a promising adsorbent for Cr(VI) ions removal Hsini, Abdelghani; Naciri, Yassine; Laabd, Mohamed; Bouzıanı, Asmae; Navío, J.A.; Puga, F.; Boukherroub, Rabah; Lakhmiri, Rajae; Albourine, Abdallah (2021-10-01) In the current study, an in-situ oxidative polymerization method was used to synthesize polyaniline-coated tungsten trioxide biphasic composite (PANI@WO3). The as-developed composite material properties were elucidated using different characterization tools such as X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), N2 sorption-desorption isotherm, and X-ray photoelect...
Investigation of HMO spectra of Huckel and Mobius type cyclacenes Turker, L; Erkoç, Şakir (1997-01-01) The Huckel molecular orbital spectra (HMO) of Huckel- and Mobius-type cyclacenes having 3-15 benzenoid rings were investigated and it was found that certain eigenvalues are topologically invariant, whereas others exhibit topological periodicity. Fbr example, Huckel-type cyclacenes having 2r (r: 2,3,4,...) benzenoid rings which possess nonbonding molecular orbitals (NBMO) and are thus expected to be open shell structures.

Citation Formats

N. K. Çokol, “Development of the methodology for the synthesis of bis-aminoinositols,” M.S. - Master of Science, Middle East Technical University, 2011.