Regio- and stereospecific synthesis of rac -carbasugar-based cyclohexane pentols Investigations of their α - and β -glucosidase inhibitions
 
Yazarlar (5)
Emel Karakılıç
Sakarya Üniversitesi, Türkiye
Sümeyye Durmuş
Sakarya Üniversitesi, Türkiye
Sedat Sevmezler
Sakarya Üniversitesi, Türkiye
Prof. Dr. Onur ŞAHİN Sinop Üniversitesi, Türkiye
Prof. Dr. Arif Baran Sakarya Üniversitesi, Türkiye
Makale Türü Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı Bioorganic and Medicinal Chemistry (Q1)
Dergi ISSN 0968-0896 Dergi Bilgileri (2018)
Dergi Tarandığı Indeksler SCI
Makale Dili İngilizce Basım Tarihi 08-2018
Kabul Tarihi Yayınlanma Tarihi 01-08-2018
Cilt / Sayı / Sayfa 26 / 14 / 4276–4287 DOI 10.1016/j.bmc.2018.07.021
Makale Linki https://linkinghub.elsevier.com/retrieve/pii/S0968089618310265
UAK Araştırma Alanları
Yoğun Madde Fiziği
Özet
In the present study, (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran was submitted to photooxygenation and two isomeric hydroperoxides were successfully obtained. Without any further purification, reduction of the hydroperoxides with titanium tetraisopropoxide catalyzed by dimethyl sulfide gave two alcohol isomers in high yields. After acetylation of alcohol with Ac2O in pyridine, epoxidation reaction of formed monoacetates with m-CPBA, then chromatographed and followed by hydrolysis of the acetate groups with NH3 in CH3OH resulted in the formation of epoxy alcohol isomers respectively. These epoxy alcohol isomers were subjected to trans-dihydroxylation reaction with acid (H2SO4) in the presence of water to afford triols. Acetylation of the free hydroxyl groups produced benzofuran triacetates in high yields. Ring-opening reaction of furan triacetates with sulfamic acid catalyzed in the presence of acetic …
Anahtar Kelimeler
Biological activity | Carbasugar | Cyclitol | “ene” Reaction