Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

Date

2009-01-02

Author

Baran, Arif
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

198
views

0
downloads

For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

Subject Keywords

COST-EFFECTIVE CATALYST, STEREOSPECIFIC SYNTHESIS, FACIAL SELECTIVITY, SCYLLO-INOSITOL, SULFAMIC ACID, MUCO-INOSITOL, CONDURITOL-F, L-CHIRO, TRISPHOSPHATE, DERIVATIVES

URI

https://hdl.handle.net/11511/57683

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo801344f

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton BARAN, ARİF; Bekarlar, Merve; Aydin, Gokay; NEBİOĞLU, MEHMET; ŞAHİN, Ertan; Balcı, Metin (2012-02-03) 1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechan...
Synthesis of ferrocenyl quinones and ferrocenyl based burning rate catalysts Açıkalın, Serdar; Zora, Metin; Department of Chemistry (2003) Recently, considerable interest has been devoted to the synthesis of new ferrocene derivatives since properly functionalized ferrocene derivatives could be potential antitumor substances. For this purpose, we have investigated the synthesis of ferrocenyl quinones starting from squaric acid. Thermolysis of ferrocenylsubstituted cyclobutenones, which have been prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl c...
Auxiliary mediated synthesis of aziridine 2 carboxylic acid derivative GARNER, Philip; Doğan, Özdemir; PİLLAİ, Satish (1994-03-01) A convenient protocol for the asymmetric synthesis of stereodefined aziridine-2-carboxylic acid derivatives from alpha,beta-unsaturated acryloyl- and crotonoyl camphor sultams is reported.
Dimethyl Ether Synthesis over Novel Silicotungstic Acid Incorporated Nanostructured Catalysts Ciftci, Aysegul; VARIŞLI, DİLEK; Doğu, Timur (2010-01-01) Dimethyl ether (DME), which is an excellent green diesel-fuel alternate with excellent clean burning properties, is synthesized by dehydration of methanol over novel solid acid catalysts, which are synthesized following a direct hydrothermal route and using silicotungstic acid (STA) as the active compound. These mesoporous silicate structured catalysts have surface area values of 108-393 m(2)/g, depending upon their W/Si ratio. These catalysts showed very high methanol dehydration activity and also very hig...
Activated carbon-tungstophosphoric acid catalysts for the synthesis of tert-amyl ethyl ether (TAEE) Obali, Zeynep; Doğu, Timur (2008-05-01) Catalytic activities of bulk tungstophosphoric acid (HPW) and its supported forms on activated carbon were investigated in the vapor phase etherification reaction of isoamylene with ethanol in a continuous flow reactor. Tungstophosphoric acid (H3PW12O40 center dot 11H(2)O) was supported on activated carbon having a surface area of 796 m(2)/g, at two different loading levels (25% and 31%) by aqueous impregnation technique and the kinetic experiments were done in a temperature range between 353 and 370 K. Sup...

Citation Formats

A. Baran and M. Balcı, “Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors,” JOURNAL OF ORGANIC CHEMISTRY, pp. 88–95, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57683.