Stereoselective synthesis of deoxycarbaheptopyranose derivatives 5a carba 6 deoxy DL galacto heptopyranose and 5a carba 6 deoxy DL gulo heptopyranose
Yazarlar (6)
Atatürk Üniversitesi, Türkiye
Middle East Technical University (Metu), Türkiye
Atatürk Üniversitesi, Türkiye
Prof. Dr. Aslıhan GÜNEL
Kırşehir Ahi Evran Üniversitesi, Türkiye
Atatürk Üniversitesi, Türkiye
Middle East Technical University (Metu), Türkiye
| Makale Türü |
Özgün Makale
(SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
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| Dergi Adı | Tetrahedron | ||
| Dergi ISSN | 0040-4020 Wos Dergi Scopus Dergi | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | İngilizce | Basım Tarihi | 01-2011 |
| Cilt / Sayı / Sayfa | 67 / 6 / 1193–1200 | DOI | 10.1016/j.tet.2010.11.102 |
| Makale Linki | https://hdl.handle.net/11511/56924 | ||
| Özet |
| Two new deoxycarbaheptopyranoses, 5a-carba-6-deoxy-α-dl-galacto- heptopyranose and 5a-carba-6-deoxy-α-dl-gulo-heptopyranose were prepared starting from cyclohexa-1,4-diene. The addition of dichloroketene to cyclohexa-1,4-diene followed by the subsequent reductive elimination and Baeyer-Villiger oxidation in turn led to the formation of a bicyclic lactone. Reduction of the lactone moiety followed by acetylation gave a diacetate with cis-configuration. The introduction of additional acetate functionality into the molecule was achieved by singlet oxygen ene-reaction. The formed hydroperoxide was reduced and then acetylated. The triacetate was further functionalized either by direct cis-hydroxylation using OsO4 or by epoxidation followed by a ring-opening reaction to give the title heptopyranose derivatives. One of the synthesized molecules, galacto-heptopyranose exhibited enzyme specific inhibition against α-glycosidase. On the other hand, they did not show any inhibition for α-amylase. However, both compounds, gulo-heptopyranose and galacto-heptopyranose increased the activity of α-amylase. © 2010 Elsevier Ltd. All rights reserved. |
| Anahtar Kelimeler |
| Carbapyranose | Carbasugar | Cyclitol | Deoxycarbasugar | Heptopyranose | Inositol |
Science Direct
Stereoselective synthesis of deoxycarbaheptopyranose derivatives 5a carba 6 deoxy DL galacto heptopyranose and 5a carba 6 deoxy DL gulo heptopyranose
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| SCOPUS | 15 |
| Google Scholar | 32 |